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Published on 19 August 2014 on http://pubs.rsc.org | doi:10.1039/9781782621355-FP001
Enantioselective Multicatalysed Tandem Reactions

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RSC Catalysis Series
Editor-in-Chief:
Professor James J Spivey, Louisiana State University, Baton Rouge, USA
Series Editors:
Professor Chris Hardacre, Queen’s University Belfast, Northern Ireland
Professor Zinfer Ismagilov, Boreskov Institute of Catalysis, Novosibirsk, Russia
Professor Umit Ozkan, Ohio State University, USA
Titles in the Series:

1: Carbons and Carbon Supported Catalysts in Hydroprocessing
2: Chiral Sulfur Ligands: Asymmetric Catalysis
3: Recent Developments in Asymmetric Organocatalysis
4: Catalysis in the Refining of Fischer–Tropsch Syncrude
5: Organocatalytic Enantioselective Conjugate Addition Reactions:
A Powerful Tool for the Stereocontrolled Synthesis of Complex Molecules
6: N-Heterocyclic Carbenes: From Laboratory Curiosities to Efficient
Synthetic Tools
7: P-Stereogenic Ligands in Enantioselective Catalysis
8: Chemistry of the Morita–Baylis–Hillman Reaction
9: Proton-Coupled Electron Transfer: A Carrefour of Chemical Reactivity
Traditions
11:13:56.
10: Asymmetric Domino Reactions

11: C-H and C-X Bond Functionalization: Transition Metal Mediation
12: Metal Organic Frameworks as Heterogeneous Catalysts
13: Environmental Catalysis Over Gold-Based Materials
14: Computational Catalysis
15: Catalysis in Ionic Liquids: From Catalyst Synthesis to Application
16: Economic Synthesis of Heterocycles: Zinc, Iron, Copper, Cobalt,
Manganese and Nickel Catalysts
17: Metal Nanoparticles for Catalysis: Advances and Applications
18: Heterogeneous Gold Catalysts and Catalysis
19: Conjugated Linoleic Acids and Conjugated Vegetable Oils
20: Enantioselective Multicatalysed Tandem Reactions
How to obtain future titles on publication:

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Enantioselective Multicatalysed
Tandem Reactions
Hélène Pellissier
CNRS and Aix Marseille Université, Centrale Marseille, Marseille, France
Email: h.pellissier@univ-amu.fr
11:13:56.
Published on 19 August 2014 on http://pubs.rsc.org | doi:10.1039/9781782621355-FP001 View Online
RSC Catalysis Series No. 20
Print ISBN: 978-1-84973-988-7

PDF eISBN: 978-1-78262-135-5
ISSN: 1757-6725
A catalogue record for this book is available from the British Library
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r Hélène Pellissier 2014
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Preface
Although asymmetric synthesis is sometimes viewed as a subdiscipline of

organic chemistry, actually this topical field transcends any narrow classi-
fication and pervades essentially all chemistry.1 Indeed, the preparation of
chiral compounds is an important and challenging area of contemporary
synthetic organic chemistry, mainly in connection with the fact that most
natural products are chiral and their physiological or pharmacological
properties depend upon their recognition by chiral receptors.2 The broad
utility of synthetic chiral molecules in medicines and materials has made
asymmetric catalysis a prominent area of investigation. Indeed, of the
methods available for preparing chiral products, catalytic asymmetric syn-
11:13:57.
thesis has attracted most attention. In particular, asymmetric transition

metal catalysis has emerged as a powerful tool to perform reactions in a
highly enantioselective fashion over the past few decades in spite of the
common drawbacks of metals, such as moisture sensitivity, recoverability,
and toxicity, particularly for heavy metals.3 Indeed, it is traditionally as-
sumed that catalysis has been the realm of metals. While the end of the last
century has been dominated by the use of metal1,4 and also biocatalysis,5 a
change in perception occurred during the last decade when several reports
confirmed that relatively simple organic molecules, such as proline, could be
highly effective and remarkably enantioselective catalysts of a variety of
fundamentally important transformations.6 This rediscovery has initiated an
explosive growth of research activities in organocatalysis, both in industry
and in academia. Organocatalysts have several important advantages, since
they are usually robust, inexpensive, readily available, and non-toxic.
Enantioselective organocatalytic processes have reached maturity in recent
years with an impressive and steadily increasing number of works regarding
the applications of this type of reaction, which paint a comprehensive pic-
ture of their real possibilities in organic synthesis.7 Hence, the application of

By Hélène Pellissier
Published by the Royal Society of Chemistry, www.rsc.org
v
View Online
vi Preface
chiral organocatalysts has permitted the preparation of a number of very

valuable chiral products with the exclusion of any trace of hazardous metals
and with several advantages from an economical and environmental point of
view.8 The ability of organocatalysts to promote a wide range of reactions by
different activation modes makes organocatalysis ideal for its application in
tandem reactions, which proceed in a one-pot procedure to build complex

frameworks from simple starting compounds. These organocatalysed one-
pot reactions are often highly efficient and follow, in some way, different
biomimetic pathways, with the same principles that are found in bio-
synthesis in nature. Chemists have devoted more and more effort to the
development of new and powerful strategies in tandem reactions that avoid
the use of costly and time-consuming protection–deprotection processes, as
well as purification procedures of intermediates. The efficiency of these
processes can be evaluated by the bonds formed, the stereoselectivity
achieved and the complexity of the newly formed molecules. Tandem cata-
lysed reactions refer to the synthetic strategies of modular combination of
catalytic reactions into one synthetic operation, occurring one after the other
and working in conjunction with each other with minimum workup or
change in conditions. Compared with stepwise synthesis, tandem reactions
avoid time, energy, and yield losses associated with the isolation and puri-
fication of intermediates. Furthermore, they help lower the risk in the
storage, transportation, and handling of toxic, unstable, or explosive inter-
mediates. Tandem reactions include one-, two-, and multicomponent
11:13:57.
domino reactions,9 which have been defined by Tietze and co-workers as

reactions involving two or more bond-forming transformations, taking place
under the same reaction conditions, without adding additional reagents and
catalysts, and in which the subsequent reactions result as a consequence of
the functionality formed by bond formation or fragmentation in the previous
step.10 It must be recognised that a relatively narrow distinction exists be-
tween domino and consecutive cascade or tandem reactions. From the point
of view of an operator, the only difference between the two lies in the point
along the sequence at which one or more catalysts (or reagents) had to be
added to effect either the initiation of a sequence (that is, domino reaction)
or propagation to the next step (that is, consecutive or tandem reaction).
Tandem catalysis refers to the synthetic strategies of modular combination
of catalytic reactions into one synthetic operation with minimum workup or
change in conditions. The use of tandem reactions in organic synthesis is
increasing constantly, since they allow the synthesis of a wide range of
complex molecules, including natural products and biologically active
compounds in an economically favourable way.11 Indeed, decreasing the
number of laboratory operations required and the quantities of chemicals
and solvents used have made tandem reactions unavoidable processes. The
proliferation of these reactions is evidenced by the number of recent reviews
covering the literature since 1986.9,12 In the last few years, an explosive
number of multiple-catalyst systems for various organic transformations
have been developed.13 The driving force in combining catalysts is to
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Preface vii
discover more efficient approaches for complex molecule synthesis with

good chemo- and stereoselectivity inaccessible through the use of single
specific catalytic systems. With increasing attention being given to this new
area, momentous chemical transformations are being discovered. It must be
noted that this novel methodology is particularly adapted to enantioselective
tandem reactions, allowing a rapid and economic construction of highly

functionalised chiral molecules from simple and readily available starting
materials in one pot. A reaction catalysed by multiple catalysts (two or three
organocatalysts, two metals, two (or more) enzymes, a metal and an orga-
nocatalyst, a metal and enzyme(s), or an organocatalyst and enzyme(s) at the
same time can allow a reactivity and a selectivity to be achieved otherwise
not possible by using a single catalyst alone. The main problem, however,
lies in finding the proper catalyst which should not only be compatible with
the other catalysts but also tolerate reagents, solvent and intermediates
generated during the course of the reaction. Unlike in biological processes in
which nature takes advantage of enzyme architecture to facilitate a multiple
reaction manifold, it is very difficult to exploit such a process in one pot. For
example, chiral metal catalysts are generally sensitive to species with co-
ordinating ability in the reaction media, while organocatalysts are relatively
robust and have high compatibility and, moreover, some organocatalysts can
promote several types of reactions through different activating modes. The
event of coordination between the two catalysts can occasionally be avoided,
for example by their sequential addition to the reaction media (sequential
11:13:57.
catalysis). In general, the use of multiple catalyst systems enlarges the sub-
strate and reaction scope for the reaction design, improves the reactivity,
and benefits the control of the selectivity. The goal of this book is to provide
researchers and professionals in academic and industrial laboratories with a
broad overview of all the developments in multicatalysed enantioselective
tandem reactions. It is divided into two sections, dealing with asymmetric
tandem reactions catalysed by multiple catalysts from the same discipline in
the first one, and asymmetric tandem reactions catalysed by multiple cata-
lysts from different disciplines in the second one. The first section is sub-
divided into five chapters, dealing successively after an introduction
(Chapter 1) with reactions catalysed by multiple organocatalysts (Chapter 2),
reactions catalysed by two metals (Chapter 3), and multienzyme-catalysed
reactions (Chapter 4), followed by conclusions (Chapter 5). The second
section of the book, which concerns tandem reactions catalysed by multiple
catalysts from different disciplines, is also divided into five chapters, dealing
successively after an introduction (Chapter 6) with reactions catalysed by a
combination of metals and organocatalysts (Chapter 7), reactions catalysed
by a combination of metals and enzymes (Chapter 8), and finally reactions
catalysed by a combination of organocatalysts and enzymes (Chapter 9),
followed by conclusions (Chapter 10). The two catalysts can interact in a
cooperative, relay or sequential manner; these three types of catalysis will be
treated successively in most of the sections of the book. In cooperative
catalysis, both the two catalysts are present at the onset of the reaction, and
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viii Preface
share the same catalytic cycle, activating two different functional groups
cooperatively to achieve the bond-formation steps. On the other hand, in
relay or sequential catalysis, the substrate first reacts with one catalyst to
give an intermediate through a first catalytic cycle. Then, this former inter-
mediate reacts with the second catalyst to provide, through a second cata-
lytic cycle, the final product or an intermediate for subsequent

transformations. The difference between relay and sequential catalysis
consists of the presence or not of the two catalysts at the onset of the re-
action. Thus, relay as well as sequential catalysis involves a set of reactions
independently catalysed by two catalysts in a consecutive manner but, while
in relay catalysis the two compatible catalysts are both present from onset, in
sequential catalysis the addition of the second catalyst during the course of
the reaction is necessary to avoid compatibility issues.
Hélène Pellissier
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Chem., 2010, 2999–3025; (f) M. Rueping, R. M. Koenigs and I. Atodiresei,
Chem. – Eur. J, 2010, 16, 9350–9365; (g) J. Zhou, Chem. – Asian J., 2010, 5,
422–434; (h) L. M. Ambrosini and T. H. Lambert, ChemCatChem, 2010, 2,
1373–1380; (i) S. Piovesana, D. M. Scarpino Schietroma and M. Bella,
Angew. Chem., Int. Ed., 2011, 50, 6216–6232; (j) N. T. Patil, V. S. Shinde
and B. Gajula, Org. Biomol. Chem., 2012, 10, 211–224; (k) A. E. Allen and
D. W. C. MacMillan, Chem. Sci., 2012, 3, 633–658; (l) Z. Du and Z. Shao,
Chem. Soc. Rev., 2013, 42, 1337–1378.
11:13:57.
11:13:57.
Contents
Abbreviations xvii
Section I Asymmetric Tandem Reactions Catalysed by

Multiple Catalysts from the Same Discipline
Chapter 1 Introduction 3
Chapter 2 Reactions Catalysed by Multiple Organocatalysts 5
2.1 Introduction 5
11:13:58.
2.2 Cooperative Catalysis 6

2.3 Relay Catalysis 20
2.4 Sequential Catalysis 32
References 43
Chapter 3 Reactions Catalysed by Two Metals 46
3.1 Introduction 46
References 58
Chapter 4 Multienzyme-Catalysed Reactions 60
4.1 Introduction 60

xiii
View Online
xiv Contents
4.2 Multienzymatic Synthesis of Chiral Alcohols 61
4.2.1 Deracemisation of Alcohols via
Stereoinversion 61
4.2.2 Multienzymatic Cascade Reactions 63
4.3 Multienzymatic Synthesis of Chiral Amines and
Amino Acids 64
4.3.1 Synthesis of Chiral Amines with
o-Transaminases 64
4.3.2 Synthesis of Chiral Amino Acids with
a-Transaminases 66
4.3.3 Synthesis of Chiral Amino Acids with
Other Enzymes 68
4.4 Other Multienzymatic Reactions 71
References 81
Chapter 5 Conclusions 85
Section II Asymmetric Tandem Reactions Catalysed by

Multiple Catalysts from Different Disciplines
Chapter 6 Introduction 89
11:13:58.
References 89
Chapter 7 Reactions Catalysed by a Combination of Metals and

Organocatalysts 91
7.1 Introduction 91
References 158
Chapter 8 Reactions Catalysed by a Combination of Metals and

Enzymes 162
8.1 Chemoenzymatic Reactions Not Based

on DKR 162
8.2 Chemoenzymatic Reactions Based on DKR 166
8.2.1 Ruthenium and Enzyme-Catalysed
DKRs 167
8.2.2 Enzymatic DKRs using Metals other than
Ruthenium 198
References 210
View Online
Contents xv
Chapter 9 Reactions Catalysed by a Combination of Organocatalysts
and Enzymes 217
References 222
Chapter 10 Conclusions 223
General Conclusion 224
Subject Index 226

11:13:58.
11:13:58.
Abbreviations
AADH amino acid dehydrogenase

AAO amino acid oxidase
Acac acetylacetone
ADCA 7-aminodesacetoxycephalosporanic acid
ADH alcohol dehydrogenase
ADP adenosine diphosphate
Aib a-aminoisobutyric acid
AIBN 2,2 0 -azobisisobutyronitrile
Ala alanine
AlaDH alanine dehydrogenase
11:13:59.
AP acid phosphatase
aq aqueous
AQN anthraquinone
Ar aryl
Asp aspartate
AspAT aspartate transaminase
ATP adenosine triphosphate
BCAAT branched amino acid transaminase
BDHP 1,1 0 -binaphth-2,2 0 -diyl hydrogen phosphate
BEMP tert-butylimino-2-diethylamino-1,3-dimethylperhydro-
1,2,3-diazaphosphorine
BINAP 2,2 0 -bis(diphenylphosphino)-1,1 0 -binaphthyl
BINIM binapthyldiimine
BINOL 1,1 0 -bi-2-naphthol
Biphep 2,2 0 -bis(diphenylphosphino)-1,1 0 -biphenyl
BMIm 1-butyl-3-methylimidazolium
Bn benzyl
Boc tert-butoxycarbonyl

xvii
View Online
Reactions Catalysed by Multiple Organocatalysts 9
enantioselectivities (75–95% ee), as shown in Scheme 2.3. A hypothetical

mechanism is depicted in Scheme 2.3 in which the chiral primary amine was
an effective catalyst for the formation of the iminium from the enone. This
iminium could be stabilised through hydrogen-bonding with the chiral
phosphoric acid. Then, the higher reactivity of this iminium was used to
Published on 19 August 2014 on http://pubs.rsc.org | doi:10.1039/9781782621355-00005
facilitate the Michael reaction between the enone and malononitrile to

produce the corresponding enamine intermediate, and the final products
were obtained from the following Knoevenagel condensation (R2 ¼ Me) and
the nucleophilic addition of the phenolic OH group on the cyano moiety and
proton transfer. On the other hand, when the iminium intermediate bore a
bulkier imine moiety (R2 ¼ Et, Ar), ketones were obtained instead of the
alkylidene malononitriles arising from Knoevenagel condensation under the
same reaction conditions.
In 2009, Bella et al. reported a formal [4 þ 2] cycloaddition of substituted
arylacetaldehydes and 2-cyclohexen-1-one which was promoted by a chiral
thiazolidine catalyst and chiral quinine via enamine formation and spon-
taneous intramolecular aldol reaction (Scheme 2.4).6 The stereoselection
depended upon the secondary amine catalyst, whereas the secondary cata-
lyst was involved in the enhancement of the nucleophilicity of the derived
enamine, probably through deprotonation of the carboxylic group. There
11:14:01.
H
HO N
H
MeO
N
(25 mol %)
S
O CO2 H
N
H OH
(25 mol %) Ar O
+ veratrol
CHO
20-41%
Ar d e > 82%
ee = 72-90%
S S
B*
CO2 H N CO2 -
N O +
B*H
Ar Ar
Scheme 2.4 Domino Michael–aldol reaction catalysed by a combination of a chiral

thiazolidine catalyst and chiral quinine.
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The Project Gutenberg eBook of Carità
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Title: Carità
Author: Mrs. Oliphant
Release date: November 25, 2023 [eBook #72221]
Language: English
Original publication: London: John Murray, Albemarle Street, 1885
Credits: Chuck Greif and the Online Distributed Proofreading Team at

http://www.pgdp.net (This file was produced from images
available at The Internet Archive)
*** START OF THE PROJECT GUTENBERG EBOOK CARITÀ ***

‘But nothing shall stand between us any more.’
CARITÀ
BY MRS. OLIPHANT
AUTHOR OF “WITHIN THE PRECINCTS,” ETC.
CHEAP EDITION
LONDON
JOHN MURRAY, ALBEMARLE STREET, W.
1885
All Rights Reserved

CONTENTS.
CHAPTER PAGE
I. The Beresfords 1
II. A Fright 10
III. Honeymooning 18
IV. The Three Charities 26
V. Coming Home 35
VI. The Consultation 44
VII. The Catastrophe 53
VIII. Consolation 62
IX. The Hill 71
X. The Square 80
XI. Mrs. Meredith 88
XII. The House next Door 98
XIII. The Young People 107
XIV. The Old People 117
XV. Roger 126
XVI. Sunday Evening 135
XVII. Edward 145
XVIII. Telling Tales 155
XIX. The Holy Inquisition 164
XX. The Perugino 173
XXI. A Confidence 183
XXII. Mystified 193
XXIII. A Remonstrance 202
XXIV. On the Other Side of the Wall 212
XXV. An Idealist 222
XXVI. In the ‘House’ 231
XXVII. The Wolf in Sheep’s Clothing 241
XXVIII. The Fireside 251
XXIX. The Old Folk and the Young 261
XXX. A Rebellious Heart 269
XXXI. The House of Mourning 279
XXXII. Taking up Dropt Stitches 288
XXXIII. Little Emmy’s Visitors 297
XXXIV. The Widow 308
XXXV. Roger’s Fate 317
XXXVI. Between the Two 326
XXXVII. The Crisis Approaching 336
XXXVIII. The Supreme Moment 346
XXXIX. The Hand of Fate 355
XL. Two—Parted 364
XLI. Two—To be One? 373
XLII. A Great Revolution 382
XLIII. The Worst Scrape of All 393
XLIV. Clearing Up 402
XLV. Conclusion 412
CARITÀ.
CHAPTER I.
THE BERESFORDS.
James Beresford and Annie his wife had been married for more than a
dozen years—their only child, indeed, had nearly attained the age of twelve
at the time when this history begins. They had both got footing on that
plateau of middle age which, if it comes to something like level ground at
thirty, need not think of a descending step for twenty years—the time of the
greatest enjoyments and most solid progress of life. He was at one end and
she at the other of the first decade; the one approaching the forties, the other
scarcely well out of the twenties; both ready to laugh at the advance of years,
which was as yet but a joke to them, and neither having thought of bidding
any grave farewell to youth. She was impulsive, enthusiastic and nervous; he
philosophical and speculative, a man ready to discuss any theory in earth or
heaven, and without any prejudices such as might make one subject of
discussion appear less legitimate than another. They were not very rich, but
neither were they poor in any sense of the word. He had been called to the
Bar, but had never gone any further in that career. They had enough between
them to live on without show, but without pinching, as so many people of
quietly social, semi-literary tastes do in London. They knew a number of
people. They saw all the pictures, read all the books, and heard all the music
that was going; not absorbed in any art, but with just enough devotion to all
to make their life full and pleasant. And there could scarcely be a pleasanter
life. The fantasies of youth, but not the sentiment of youth, had ended for
both. Mr. Beresford had some mildly scientific pursuits, was a member of
some learned societies, and of one or two new and advanced clubs where
clever men were supposed to abound. Occasionally in his comfortable
library he wrote an article for a review or magazine, which was very much
talked about by his friends, to the great edification and amusement of people
who live by writing articles and say nothing about them. This gave him an
agreeable sense of duty to add seriousness to his life; and he was never
without occupation—meetings of committees, scraps of semi-public
business, educational and other projects, which, for the moment at least,
seemed full of interest to the world, made him feel himself a not
unimportant, certainly not a useless, man. Mrs. Beresford, on her side, had
the natural occupation of her housekeeping, and her child, whose education
gave her much thought—so much thought that many people with full
nurseries listened with a certain awe to her ideas of all that was necessary for
her little girl, and sighed to think how much less was possible when there
were six or seven little girls to think of.
The child, however, was not so over-educated and over-cared for as might
have been fancied; for the parents were young, as has been said, very fond of
each other, and fond of their own way; which likings did not consist with the
burden of dragging a small child with them wherever they went. The
Beresfords liked to go about ‘honeymooning,’ as their friends called it, and
as they themselves were not displeased to call it, by themselves, over the
world. They would start sometimes quite suddenly, to the Riviera in the
middle of winter, to escape London fogs and wintry chills; to Paris at Easter;
to Scotland in the autumn; even to Norway sometimes, or such difficult
places; and it stood to reason that they could not take the child with them
when they started at a day’s notice on these delightful journeys. For their
journeys were delightful. They were well enough off not to require to count
the cost; they went lightly, with little luggage and no servants, and they went
everywhere together. But it would have been bad for the little girl; therefore
she stayed at home, under the care of the best of nurses, who had been Mrs.
Beresford’s nurse before the child’s; and the father and mother, like two
lovers, roamed lightly about the world. But when they were at home, Mrs.
Beresford talked a great deal about education, and had plans enough to have
educated six princesses, let alone one little girl of undistinguished lineage. It
was a very lucky thing for all parties, their friends said, that they had but this
one child. Had they been hampered by half-a-dozen, what could they have
done? It would have changed their life completely. And one of their many
felicities was, that whereas they were preserved from the old-maidishness of
childless married persons by having a child, their freedom of action was
preserved by the fact that they had but one.
And they were wonderfully free of other relations who might have
hampered them. Mrs. Beresford had been an orphan from her childhood,
brought up by her grandmother, who in the course of nature was dead too;
and Mr. Beresford’s only two relations were a wealthy aunt, Charity
Beresford, who lived in a pretty house in the country, within driving distance
of London, and with whom lived his elder sister, Cherry Beresford, named
after her aunt, and living in considerable subjection to that energetic woman.
Miss Beresford was the richest member of the family, and her nephew had
expectations from her; and Charity was the favourite female name of this
branch of the race. But the idea of calling her child Charity did not at all
smile upon young Mrs. Beresford when her baby was born. She was
beguiled, however, by the unusual look of it, which charmed her, into calling
the little girl by the more melodious name of Carità, contracted prettily into
Cara in the drawing-room, and Carry in the nursery. Aunt Charity growled
when she heard of this, but did not otherwise complain, and gentle Aunt
Cherry declared herself unfeignedly glad that her little niece had thus
escaped the worse consequences of a symbolical name. When the young
couple went away pleasuring, little Cara very often would be sent to
Sunninghill, to pass the quiet days there under the charge of the aunts; and
so all responsibility was removed from the minds of the parents. They had a
letter sent to them every day to assure them of their welfare, however far off
they might go—an extravagance which Aunt Charity condemned loudly, but
which Aunt Cherry was proud of, as showing the devotion of the parents to
little Cara. The child herself was very happy at Sunninghill, and was a much
more prominent person there than at home, where very often she was in the
way, and interrupted conversation. For a father and mother who are very
fond of each other, and have a great deal to talk of, often, it must be allowed,
are hampered by the presence of one curious child, with quick ears and an
inconveniently good memory. In this particular the half-dozen would have
been more easily managed than the one.
Thus the Beresfords led a very pleasant life. They had the prettiest house;
naturally, travelling so much as they did, they had been able to ‘pick up’ a
great many charming things. You could scarcely see their walls for pictures;
some very good, one or two wonderful windfalls, and the rest pretty enough;
nothing strikingly bad, or next to nothing. Where other people had ordinary
china, they had genuine old faïence, and one or two plaques which Raphael
himself might have seen perhaps—Urbino ware, with Messer Giorgio’s
name upon it. Not to speak of the Venice point which Mrs. Beresford wore,
there were brackets in the drawing-room hung with scraps of old point coupé
which many a lady would have been glad to trim her dress with; and, instead
of common portières, they had two pieces of old tapestry from an Italian
convent which devotees went down on their knees before. But I have not
space to tell you how many pretty things they had. It was one of the
pleasures of their life whenever they saw anything that pleased them to bring
it home for the decoration of that pretty drawing-room, or the library, which
Mr. Beresford had filled with old vellum-bound volumes of curious editions,
and pretty books in Russian leather which kept the room always fragrant.
What was wanting to this pleasant, warm, full, delightful living? Nothing but
continuance; and it had not struck either of them that there was any doubt of
this for long, long years at least. What a long way off threescore years and
ten look when you are not yet forty! and death looked further off still.
Neither of them thought of dying. Why should they? For, to be sure, though
we know very well that must happen to us some time, in our hearts we are
incredulous, and do not believe that we ever can die. The Beresfords never
dreamt of anything so frightful. They were well, they were happy, they were
young; and as it had been, so it would be; and a world so bright they felt
must mean to go on for ever.
When Cara was about ten, however, the mother began to feel less well
than usual. There was nothing much the matter with her, it was thought:
want of ‘tone,’—a little irritability of disposition—a nervous temperament.
What she wanted was change of air and scene. And she got that, and got
better, as was thought; but then became ill again. No, not ill—unwell,
indisposed, mal à son aise, nothing more. There was nothing the matter with
her really, the doctors thought. Her lungs and her heart, and all vital organs,
were perfectly sound; but there was a little local irritation which, acting upon
a nervous temperament—— The nervous temperament was perpetually kept
in the front, and all sorts of evils imputed to its agency. At Sunninghill, it
must be confessed, they did not believe in the illness at all.
‘Fudge,’ said Aunt Charity, who had always been strong, and had no faith
in nerves, ‘don’t talk to me of your nervous temperaments. I know what it
means. It means that Annie has fallen sick of always having her own way.
She has everything she can desire, and she is ill of having nothing more to
wish for. A case of Alexander over again in a London drawing-room—that’s
what it is, and nothing else, my word upon it; and I know my niece.’
‘Yes, Mr. Maxwell; perhaps there is some truth in what Aunt Charity
says,’ said Miss Cherry. ‘I think you know I don’t judge harshly——’
‘That means that I judge harshly,’ said Miss Charity, bursting in; ‘thank
you, my dear. Well, you may call me uncharitable if you please; but there’s
where it is; let James lose the half of his fortune, or all his china get broken,
and she’d come round in no time—that’s what ails Annie. But as she belongs
to a very refined society, and has a silly husband, it’s called nerves. Bless
me, Cherry, I hope I knew what nerves were, and all about it, before you
were born.’
‘You could not know Annie before I was born,’ said Miss Cherry, who
was devoid of imagination. ‘I hope you will give her your best attention, Mr.
Maxwell. My brother James is a very fond husband, poor fellow! If anything
happened to Annie, he would never get the better of it. As for marrying
again, or anything of that sort——’
‘Good heavens!’ said the doctor; ‘I hope there is no need to take such an
idea into consideration. We must not go so fast.’
Miss Charity laughed. She was a great deal older than her niece, but
much more sensible. ‘There’s the seventh commandment to be thought of,’
she said; for her remarks were sometimes more free than they ought to be,
and put Miss Cherry to the blush: and this was all the worse because she
immediately walked out into the garden through the open window and left
the younger lady alone with the doctor, who was an old friend of the family,
and contemporary of the second Charity Beresford. Very old friends they
were; even it was supposed that in their youth there had been or might have
been passages of sentiment between these two now sitting so calmly
opposite each other. Mr. Maxwell, however, by this time was a widower, and
not at all sentimental. He laughed, too, as Miss Beresford made her exit by
the window. He was very well used to the family, and all its ways.
‘She wears very well,’ he said, reflectively. ‘I don’t think she has aged to
speak of for these twenty years. When I used to be coming here in my early
days, when I was beginning practice——’
‘The rest of us have changed very much since then.’
‘Yes,’ said Mr. Maxwell, thinking most of himself; ‘but she not at all. I
could think when I look at her that I was still, as I say, a young fellow
beginning practice——’
Miss Cherry sighed—very softly, but still she did sigh: over forty, but still
in the position and with many of the sentiments of a girl. People laugh at the
combination, but it is a touching one on the whole. What ages of lingering
monotonous life had passed over her since her present companion began his
practice, since her Aunt Charity had begun to be an old woman! Dr.
Maxwell had married, had lost his wife, had gone through perhaps sharper
troubles than Miss Cherry had known. He was now middle-aged and stoutish
and weather-beaten—weather-beaten in aspect and in soul—while she was
slim and soft and maidenly still. The sigh was half for those uneventful
years, and half for the undevelopment which she was conscious of—the
unchangedness of herself, underneath the outer guise, which was changed;
but this was not safe ground, nor could it be talked of. So she brushed away
the sigh with a little cough, and added quickly:
‘I know perhaps what nerves are better than my aunt does, and I know
Annie better. Tell me seriously, Mr. Maxwell, now we are alone. You don’t
apprehend anything serious? Should she go on travelling and running about
as they do if there is really anything the matter? No one can be so much
interested as I am. You would be quite frank with me?’
‘It is the best thing for her,’ said the doctor. ‘You now—I should not say
the same for you. You are a tranquil person and patient; but for her, the more
she runs about the better. It distracts her and keeps her from thinking. If she
worries, it’s all over with a woman like that.’
‘She has so little to worry about.’
‘Just so; and the less one has to bear the less one is fit for; that is to say,’
said the doctor, getting up and going to the window, ‘the less some people
are fit for. There’s that old aunt of yours to prove me a fool. She has never
had anything to bear, that I know of; and she is strong enough to bear
anything. Sixty-eight, and just look at her. There’s a physique for you—that
is the kind of woman,’ Mr. Maxwell said, with a little outburst of
professional enthusiasm, ‘that I admire—as straight as a rod still, and every
faculty in good order. That a woman like that should never have married is a
loss to the world.’
Miss Cherry, who had gone to the window too, and stood by his side,
looked out somewhat wistfully at her old aunt. Cherry was not like her, but
took after the other side of the family, her own mother, who had died young,
and had not possessed any physique to speak of. ‘It is very sweet to-day in
the garden,’ she said, inconsequently, and stepped out into the world of
flowers and sunshine. Sunninghill was an ideal house for two ladies, a place
which people who were shut out from such delights considered quite enough
for happiness. Indeed, Miss Cherry Beresford’s friends in general resented
deeply the little plaintive air she sometimes took upon her. ‘What could she
wish for more?’ they said, indignantly; ‘a place that was just too good to be
wasted on two single women. There should be a family in it.’ This was
especially the sentiment of the rector’s wife, who was a friend of Cherry’s,
and who felt it a personal slight to herself, who had a large family and many
cares, when Cherry Beresford, with not a thing in the world to trouble her,
presumed to look as if she was not quite happy. The house stood upon a hill,
fringed round with small but delightful woods. These woods were on a level
with the highest turrets of the great beautiful royal Castle of St. George,
which lay full within sight in the afternoon sunshine. So you may imagine
what a view it was that was visible from the old smooth velvet lawn round
the house, which formed the apex to these woods. The quiet plain all around
lay basking in the light underneath, and the Castle upon its hill dominated,
with a broad and placid grandeur, that majestic sweep of country, with all its
lights and shadows. The royal flag fluttered on the breeze, the great tower
rose grey and solid against the sky. Green branches framed in this picture on
every side; the cuttings in the trees made a picture-gallery indeed of different
views for different hours, according to the lights. ‘What a lovely place it is!’
Mr. Maxwell said, with sudden enthusiasm; ‘I always forget how lovely it is
till I come back.’
‘Yes, it is beautiful,’ said Cherry, who was used to it. ‘If you are going to
send them away, I suppose Cara may come to us for the summer?—that
makes such a difference.’ Cherry was very well used to the different lights.
She acknowledged the beauty of her home, and yet I can fancy
circumstances under which she would have liked a little house in a street
better. Man or woman either cannot live by beauty alone any more than by
bread.
‘Here’s a pretty business,’ said Miss Beresford, briskly; ‘half of my roses,
I believe, spoiled for this year; no second show this time. Jones is the
greatest idiot; he pretends to know everything, and he knows nothing. Your
protégé, Cherry, of course. All the incapables hang on by you.’
‘I can’t see any signs of deficiency,’ said the doctor, looking round.
‘Not at this moment; if there were, he should have his dismissal on the
spot. If those two go off again, as you are always sending them off, tell
James I insist on the child coming here. Ah! that’s what your women of
nervous temperament do—leave their children at home in a poky London
square, while they go wandering over the world. Tell them I wish it,’ said
Miss Beresford, with a laugh; ‘they never go against me.’
‘They know how kind you always are.’
‘They know I’m old and will have something to leave behind me, that’s
the plain English of it—as if I was going to accept poor Cherry’s subjection,
poor soul, without rewarding her for it! It is she who will have everything
when I’m gone. I’ve told them that, but still they think there’s a chance that
Cara might cut her old aunt out. I can see through them. I see through most
people,’ she added, with a laugh, looking at him full. How could she know
the thought passing through his mind at the moment, which was the abrupt
reflection, uncalled for perhaps, that for a professional man, who had made
no extraordinary name in his profession, Cherry Beresford, though an old
maiden, would make not such a bad wife? Could the old witch see through
broadcloth, and the comfortable coating of middle-aged flesh and blood,
straight into a man’s heart? He grew red foolishly, as if that were possible,
and stammered a little in his reply:
‘I can believe everything that is clever of you as well as everything that is
kind; though why you ladies should make such a point of having a little chit
like that, who can only disturb your quiet in this paradise of a place——’
‘Oh, how can you say so!’ said Cherry. ‘The child’s voice and the child’s
face make all the difference—they are better than sunshine. They make the
place beautiful. I would give it all, twenty times over, to have the child.’
‘Whom her mother is very glad to leave behind her.’
‘Hold your tongue, Cherry,’ said the elder lady; ‘you mild little old
maids, you are always in a way about children. I never took up that line. A
child in the abstract is a nuisance. Now, a man—there are advantages about a
man. Sometimes he’s a nuisance too, but sometimes he’s a help. Believe
them, and they’ll tell you that marriage was always far from their thoughts,
but that children are their delight. That’s not my way of thinking. But I
happen to like little Cara because she is Cara, not because she is a child. So
she may come and take her chance with the rest.’
Cherry had turned away along the garden path, and was looking through
one of the openings at one of the views. She knew it by heart—exactly how
the light fell, and where were the shadows, and the name of every tower, and
almost the shape of every cloud. Was it wonderful that this was not so
delightful to her as to the strangers who could not see that view every day in
their lives? To some people, indeed, the atmospheric changes, the effects of
wind and colour, the waverings and dispersions of those clouds, would have
made poetry enough to fill up all that was wanting; but poor Miss Cherry
was not poetical in this big way, though she was very fond of pretty verses,
and even wrote some occasionally; but how she longed for the child’s
innocent looks—the child’s ceaseless prattle! Her gentle delicacy was hurt at
that unnecessary gibe about the old-maidishness, and her supposed sham
rejection of the husband who had never come her way. ‘Why should she talk
of men—especially before him? What do I want with men?’ said poor Miss
Cherry to herself; ‘but my own niece—my brother’s child—surely I may
wish for her.’ And surely there could not have been a more innocent wish.
CHAPTER II.
A FRIGHT.
‘Which you please; you are not gouty or rheumatical, or anything of that
sort,’ said Mr. Maxwell, almost gaily. ‘Homburg, for instance—Homburg
would do—or Baden, if you prefer that. I incline to the one you prefer; and
enjoy yourself as much as you can—that is my prescription. Open air,
novelty, change; and if you find you don’t relish one place, go to another.
The sea, if you take a fancy for the sea; and Sir William is of my opinion
exactly. Choose the place which amuses you most.’
‘It seems to me,’ said Mr. Beresford, ‘that these wise men are laughing at
you, Annie. They know there’s nothing the matter with you. If I were not
much obliged to them for thinking so, I should say you had some reason to
be offended. One knows what you doctors mean when you tell a patient to
do whatever she likes best.’
‘It means one of two things,’ said Mrs. Beresford; ‘either that it is
nothing, or that it is hopeless——’
Her husband burst into a soft laugh. ‘Well,’ he said, ‘it is very evident it
cannot be the last—so it must be as I say. It is injurious to our pride, my
darling; for I allow that it is pleasant to possess either in your own person or
your wife’s a delicate and mysterious malady, of which it can be said that it
baffles the doctors, without very much hurting the patient; but never mind. If
you can bear this disrespectful verdict that you have nothing the matter with
you, I assure you it makes me quite happy.’
Mrs. Beresford looked at the doctor with very keen, eager eyes—eyes
which had grown bigger and keener of late, perhaps from the failing of the
round, smooth outlines of the face. She noticed that, though Maxwell saw
very well that she was looking at him, he did not reply to those looks, but
rather turned to her husband and answered him, as if he had not observed her
at all.
‘I don’t mean to be at all disrespectful,’ he said; ‘there is a little
disturbance of the system, which might turn to something as serious as you
could desire, and take away the comfort of life perhaps more completely
than a regular disease; but I hope that is not likely to happen here.’
‘No; I don’t think it,’ said the easy man. ‘We shall try Baden, which is the
prettiest—unless you prefer some other place; in short, we shall go off
without guide or compass, and do exactly what pleases ourselves. We have
done so, it must be allowed, pretty often before—but to do it with the
sanction of the faculty——’
‘And the child—as usual—will go to Sunninghill?’
‘Why should you say as usual, Mr. Maxwell?’ said Mrs. Beresford, with a
suspicion of offence. ‘Do you think I ought to take her with me? Do you
suppose, perhaps, that I might not come back again—that I might never—
see——’
‘This is so unnecessary,’ said the doctor, remonstrating. ‘What must I
say? I wish I was as certain of a thousand a year. You will come back quite
well, I hope.’
‘When people are very ill don’t you say much the same things to them?
There was poor Susan Maitland, whom you banished to Italy to die. People
talked of her coming back again. Oh, no! I am not thinking of myself, but of
the subject in general. One needed only to look in her face to see that she
would never come back.’
‘People have different ideas of their duty,’ said Maxwell. ‘Some think it
best not to frighten a patient with thoughts of death. I don’t know that one
can lay down any rule; one is guided by circumstances. To some nervous
people it is best not to say anything. Some are more frightened than others—
just as some people are more susceptible to pain than others.’
‘Now I am going to ask you another question,’ said Mrs. Beresford.
‘Suppose you had a patient very ill—I mean hopelessly ill, beyond all cure
—do you think it is right to keep them alive as you do now, struggling to the
last, staving off every new attack that might carry them off in quiet, fighting
on and on to the last moment, and even prolonging that, when it comes so
far, with cordials and stimulants? Keeping their breath in their poor,
suffering bodies till you get to the end of your resources—your dreadful,
cruel resources, that is what I call them. Do you think this is right? I had an
aunt who died dreadfully—of cancer——’
‘Ah! An aunt? You did not tell me this,’ said the doctor, off his guard;
then, recovering himself, with something that looked like alarm, he said,
hurriedly: ‘What would you have us do—kill the poor creatures? neglect
them? refuse what aid, what alleviations we can——’
‘I’ll tell you what I should like you to do if it were me,’ she said, eagerly.
‘When it was all over, when you were sure I could not get better, when there
was nothing more in life but to suffer—suffer: then I should like you to
make a strong, sweet dose for me to put me out of my trouble. I should like
James to give it me. Do you remember what was said that time in India, in
the mutiny? I don’t know if it was true, but people said it. That the husbands
of some of the poor ladies kissed them and shot them, to save them; don’t
you remember? That is what I should like you to do—a sweet, strong dose;
and James would bring it to me and kiss me, and put it to my lips. That
would be true love!’ she said, growing excited, the pale roses in her cheeks
becoming hectic red; ‘that would be true friendship, Mr. Maxwell! Then I
should not feel afraid. I should feel that you two stood between me and
anguish, between me and agony——’
Both the men rose to their feet as if to restrain her vehemence, with one
impulse. ‘My darling, my darling!’ said James Beresford, in dismay, ‘what
are you thinking of?’ As for Mr. Maxwell, he walked to the window and
looked out, his features working painfully. There was a moment in which the
husband and wife clung together, he consoling her with every reassuring
word that he could think of, she clinging to him with long, hysterical sobs.
‘My love, what has put this into your head?’ he said, half sobbing too, yet
pretending to laugh. ‘My Annie, what fancy is this? Have you lost your wits,
my darling? Why, this is all folly; it is a dream; it is a craze you have taken
into your head. Here is Maxwell will tell you——’
But Maxwell made him a sign over his wife’s head so impassioned and
imperative that the man was struck dumb for the moment. He gazed blankly
at the doctor, then stooped down to murmur fond words less distinct and
articulate in her ear. Fortunately, she was too much excited, too much
disturbed, to notice this sudden pause, or that the doctor said nothing in
response to her husband’s appeal. She held fast by his arm and sobbed, but
gradually grew calmer, soothed by his tenderness, and after a while made a
half-smiling, tearful apology for her weakness. It was after dinner on a
lovely summer evening, not more than twilight, though it was late. The two
gentlemen had been lingering over their claret, while she lay on the sofa
waiting for them, for she did not choose to be shut up upstairs all by herself,
she said. After she had recovered they went to the drawing-room, where the

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Enantioselective Multicatalysed Tandem Reactions

RSC Catalysis Series

Titles in the Series:

10: Asymmetric Domino Reactions

How to obtain future titles on publication:

For further information please contact:

Visit our website at www.rsc.org/books

RSC Catalysis Series No. 20

Print ISBN: 978-1-84973-988-7

r Hélène Pellissier 2014

All rights reserved

Published by The Royal Society of Chemistry,

Registered Charity Number 207890

For further information see our web site at www.rsc.org

Although asymmetric synthesis is sometimes viewed as a subdiscipline of

thesis has attracted most attention. In particular, asymmetric transition

RSC Catalysis Series No. 20

chiral organocatalysts has permitted the preparation of a number of very

tandem reactions, which proceed in a one-pot procedure to build complex

domino reactions,9 which have been defined by Tietze and co-workers as

discover more eﬃcient approaches for complex molecule synthesis with

tandem reactions, allowing a rapid and economic construction of highly

lytic cycle, the final product or an intermediate for subsequent

Asymmetric Organocatalysis—From Biomimetic Concepts to Powerful

(w) D. W. C. MacMillan, Nature, 2008, 455, 304–308; (x) X. Yu and

Tetrahedron: Asymmetry, 2007, 18, 693–700; (e) Synthesis of Heterocycles

Brasche and K. Gericke, Domino Reactions in Organic Synthesis, Wiley-

809–833; (j) E. Capdevila, J. Rayo, F. Carrion, I. Jové, J. I. Borrell and

1508; (c) D. H. Paull, C. J. Abraham, M. T. Scerba, E. Alden-Danforth and

Section I Asymmetric Tandem Reactions Catalysed by

Chapter 2 Reactions Catalysed by Multiple Organocatalysts 5

2.2 Cooperative Catalysis 6

Chapter 3 Reactions Catalysed by Two Metals 46

Chapter 4 Multienzyme-Catalysed Reactions 60

RSC Catalysis Series No. 20

Section II Asymmetric Tandem Reactions Catalysed by

Chapter 7 Reactions Catalysed by a Combination of Metals and

Chapter 8 Reactions Catalysed by a Combination of Metals and

8.1 Chemoenzymatic Reactions Not Based

Chapter 10 Conclusions 223

General Conclusion 224

Subject Index 226

AADH amino acid dehydrogenase

RSC Catalysis Series No. 20

Reactions Catalysed by Multiple Organocatalysts 9

enantioselectivities (75–95% ee), as shown in Scheme 2.3. A hypothetical

facilitate the Michael reaction between the enone and malononitrile to

Scheme 2.4 Domino Michael–aldol reaction catalysed by a combination of a chiral

Author: Mrs. Oliphant

Release date: November 25, 2023 [eBook #72221]

Original publication: London: John Murray, Albemarle Street, 1885

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