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The Growing Impact of Asymmetric Catalysis - Aldrichimica Acta Vol. 40 No. 3

The Growing Impact of Asymmetric Catalysis - Aldrichimica Acta Vol. 40 No. 3

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Palladium-Catalyzed Dynamic Kinetic Asymmetric Allylic Alkylation with the dPPBA Ligands

Development and Applications of C2-Symmetric, Chiral, Phase-Transfer Catalysts
Palladium-Catalyzed Dynamic Kinetic Asymmetric Allylic Alkylation with the dPPBA Ligands

Development and Applications of C2-Symmetric, Chiral, Phase-Transfer Catalysts

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Categories:Types, Research, Science
Published by: Sigma Aldrich Chemistry on Feb 12, 2009
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06/16/2009

 
The GrowinG impacT of asymmeTric caTalysis
VOL. 40, NO. 3 • 2007
Palladium-Catalyzed Dynamic Kinetic AsymmetricAllylic Alkylation with the DPPBA LigandsDevelopment and Applications of
C  
2
-Symmetric,Chiral, Phase-Transfer Catalysts
 
57
   V   O   L .   4   0 ,   N   O .   3  •   2   0   0   7
Aldrich Chemical Co., Inc.Sigma-Aldrich Corporation
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Editor 
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SharbilJ.Firsan,Ph.D.P.O.Box355,Milwaukee,WI53201,USA
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VOL. 40, NO. 3 • 2007
“PLEASE BOTHER US.”
Professor Carsten Bolm of RWTH Aachen University, kindly suggested that we make2-(trimethylsilyl)ethanesulfonyl chloride (SES-Cl). This reagent is employed to protect anamine in the form of its sulfonamide. In contrast to the harsh conditions sometimes neededto deprotect tosyl-protected amines, the SES group is readily cleaved under mild conditionsusing a fluoride ion source, regenerating the parent amine along with volatile byproducts.We have also prepared SES-NH
2
, a useful reagent for the introduction of a protected nitrogenatom into a substrate.
1,2
(1) Weinreb. S. M. et al.
Tetrahedron Lett.
 
1986
,
27 
, 2099. (2) Ribière, P. et al.
Chem. Rev.
2006
,
106
,2249.
SiSClOOH
3
CCH
3
H
3
CSiSNH
2
OOH
3
CCH
3
H
3
C
6813342-(Trimethylsilyl)ethanesulfonyl chloride
1 g(SES-Cl) 5 g
6813262-(Trimethylsilyl)ethanesulfonamide
1 g(SES-NH
2
)
Naturally, we made these useful reagents. It was no bother at all, just a pleasure to beable to help.
Do you have a compound that you wish Aldrich could list, and that would help you in your research by saving you time and money? If so, please send us your suggestion; we will bedelighted to give it careful consideration. You can contact us in any one of the ways shownon this page and on the inside back cover.
TABLE OF CONTENTS
Palladium-Catalyzed Dynamic Kinetic Asymmetric Allylic Alkylation with the DPPBALigands
..............................................................................................................................................................................................................................................
59
Barry M. Trost* and Daniel R. Fandrick,
Stanford University
Development and Applications of
2
-Symmetric, Chiral, Phase-Transfer Catalysts
..........
77
Takashi Ooi and Keiji Maruoka,*
Kyoto University
ABOUT OUR COVER
Oarsmen at Chatou
(oil on canvas,81.2
×
100.2 cm) was painted in 1879by the French impressionist painter,Pierre Auguste Renoir (1841–1919), onthe river Seine west of Paris. His use oflight fresh colors in this painting andthroughout his career was the result ofhis love of paintings from the Rococoperiod and of his training in a porcelainfactory as a young man.Rowing was the foremost attractionat Chatou. The man in this boat—wearing the typical costume of ashort jacket and a straw hat—may bethe artist’s brother, Edmond. The manstanding on the bank, similarly attired, is probably the painter Gustave Caillebotte, adevoted rowing enthusiast and a friend of Renoir. The woman is most likely Aline Charigot,who was his favorite model and later became his wife.The painting captures the brilliance of sun and water, summer and youth. In the water,strong blues and white alternate. Their shimmering intensity is enhanced by the equallystrong presence of orange in the boat’s reflection and the scarlet accent of Aline’s bow.Renoir has put into practice the principle of simultaneous contrast: colors are perceivedstronger when juxtaposed with their opposites—orange with blue, for example, or greenwith red. The silky texture of Renoir’s feathery brushstrokes mirrors the languid andleisurely scene.
This painting is a gift of Sam A. Lewisohn to the National Gallery of Art,Washington, DC.
J p, pdtad c c., i.
Photograph © Board of Trustees, National Gallery of Art, Washington.

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