Asymmetric Organocatalysts

Asymmetric organocatalysis has emerged as a powerful enantioselectiviy even though the time takes longer to complete
synthetic tool that is complementary to metal-catalyzed the reaction.
reactions. Pioneering work in this area dates back to the 1970s
in which Eder et al. and Hajos et al. separately reported an Br
O T3080 (5 mol%)
intramolecular asymmetric aldol reaction which employed TFA

H2O (10 eq.), acetone,

L-proline (P0481) as catalyst.1),2) This reaction was considered O O Br N O 0 oC, 9 h
H
N C NH S
to be a special case at that time. Later in 2000, List et al. H
O
S
Br O
OH
reported an L-proline-catalyzed intermolecular asymmetric T3080 CH2 C CH3

aldol reaction.3) The same year, MacMillan et al. documented Br N O Y. 99%

H 95% ee
the first highly enantioselective amine-catalyzed Diels-Alder (R)-Convolutamydine A

reaction.4) These reports received a great deal of attention and

the research in the area of asymmetric organocatalysts has Singh et al. also developed a new class of proline-based
since thrived.5) organocatalysts and reported asymmetric direct aldol reactions
with excellent enantioselectivities (>99% ee). A variety of
O O L-Proline O OH
(P0481)
ketones and aldehydes could be employed using 0.5 mol% of
(30 mol %)
H catalyst (H1407).9)
DMSO
NO2 NO2

Y. 68%, 76% ee
Singh's catalyst
H OH (H1407)
N O O O OH
N (0.5 mol%)
Later, the significance of these proline-catalyzed reactions H
O +
CH3 c-Hex H brine, -10 °C c-Hex
was luminously demonstrated by MacMillan for the application CH3
Y. 62%, >99% ee
H1407
to carbohydrate synthesis.6) Córdova et al. reported a proline- Singh's catalyst

catalyzed asymmetric conversion of protected glycol aldehydes

into hexoses in one step.7) Due to the various advantages including ready availability
and versatility, the asymmetric reactions using other amino
L-Proline
O (P0481) OH O O OH acids as organocatalysts were also intensively studied. More
(10 mol %) BnO
H H recently, the group of Lu explored the possibility of deriving a
DMF, rt, 4 d BnO OBn
OBn OBn OBn wide array of novel multifunctional organocatalysts from amino
OH
acid structural scaffolds.10) The new catalyst, dipeptide-derived
Y. 51% Y. 41%
4:1 dr, 98% ee >99% ee phosphine (T2937), was proven to promote enantioselective
[3+2] cycloadditions of allenes to acrylates or acrylamides.
Compared with conventional transition metal complex
O
catalysts, asymmetric organocatalysts offer several advantages P +
•
Ph N Ph CO2t-Bu
CH3 O Ph
including operational simplicity, their availability, and low CH3
CH3 O Si CH3 Ph
Ph CH3 CO2t-Bu
CH3 N CH3
toxicity which confer a direct benefit in the production of (CH3)3CO NH
H
PPh2
T2937 (5 mol%)
pharmaceuticals and contribution to green chemistry. O T2937 Et2O, 5 MS, 0 °C, 1 h N Ph

P
In the initial spectacular advances in asymmetric O
Ph
Ph

organocatalysis, proline and its analogues have been

predominantly employed. Generally organocatalytic aldol Cinchona alkaloids and their derivatives have been
reactions with ketones as acceptors require high catalyst intensively used as chiral ligands for metal-catalyzed reactions
loadings, however a recent development in this area enables or as organocatalysts as demonstrated in Sharpless
the reaction with a lower catalyst loading. Nakamura et al. asymmetric dihydroxylation with an OsO 4 -cinchona alkaloids
reported the enantioselective synthesis of (R)-convolutamydine complex.11) It is considered as one of the most privileged chiral
by using 5 mol% of newly developed novel N-heteroaryl- inducers. Cinchona alkaloids-derived catalysts could be
sulfonylprolinamide (T3080).8) In this reaction, amounts of the effectively applied for nearly all classes of organic reactions.
catalyst can be reduced to 0.5 mol% with retention of the The quinuclidinyl moiety as a tertiary amine could serve as an

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 Asymmetric Organocatalysts

active center for Brønsted base catalysis, Lewis base catalysis, O O

CH3 CH3
+
and nucleophilic catalysis. Upon alkylation of the quinuclidine H Ph CH3 CO2CH3
N Cl
H
nitrogen, the resulting ammonium salts could serve as phase N N CH3 O
Cl D3983 (0.5 mol%)
transfer catalysts, another class of organic catalysis. H
O . H2O Et3N (1.5 eq.) O Ph

Hatakeyama, Ishihara, et al. have developed a-isocupreine D3983

AcOEt, rt CH3 CO2CH3
Y. 88%, 99% ee
(a-ICPN, E0974), a pseudoenantiomer of b-isocupreidine
(I0728) and reported the application to an efficient asymmetric
Morita-Baylis-Hillman (MBH) reaction.12)

O CF3
CH2CH3 CHO
+ O CF3
N
CH2
O
OH O CF3
N
E0974 (0.1 eq.)
O CF3
References
OH DMF, -55 °C, 24 h
CH2
E0974
Y. 91%, 88% ee
1) U. Eder, G. Sauer, R. Wiechert, Angew. Chem. Int. Ed. 1971, 10, 496.
2) Z. G. Hajos, D. R. Parrish, J. Org. Chem. 1974, 39, 1615.
Since the pioneering work on asymmetric synthesis of amino 3) B. List, R. A. Lerner, C. F. Barbas III, J. Am. Chem. Soc. 2000, 122, 2395.
acids using N-benzyl cinchoninium halide as a chiral phase 4) K. A. Ahrendt, C. J. Borths, D. W. C. MacMillan, J. Am. Chem. Soc. 2000, 122,
transfer catalyst in 1980s,13) numerous cinchona alkaloids- 4243.
derived chiral phase-transfer catalysts have been developed.14) 5) S. Mukherjee, J. W. Yang, S. Hoffman, B. List, Chem. Rev. 2007, 107, 5471.
In the late 1990s, a totally new aspect on the design of chiral 6) A. B. Northrup, D. W. C. MacMillan, Science 2004, 305, 1752.
phase-transfer catalyst, based on the C2 -symmetrical chiral 7) A. Córdova, M. Engqvist, I. Ibraham, J. Casas, H. Sundén, Chem. Commun.
binaphthyl moiety, has emerged.15) The ongoing efforts towards 2005, 2047.
the simplification of the catalyst have led to the novel catalyst 8) S. Nakamura, N. Hara, H. Nakashima, K. Kubo, N. Shibata, T. Toru, Chem. Eur. J.
which could be employed under even milder conditions with 2008, 14, 8079.
excellent enantioselectivitities. Maruoka et al. reported an 9) (a) H. Kylmälä, A. Neuvonen, R. Jokela, Int. J. Org. Chem. 2013, 3, 162.
enantioselective conjugate addition of 3-substituted oxindoles (b) V. Maya, M. Raj, V. K. Singh, Org. Lett. 2007, 9, 2593.
to Michael acceptors under neutral conditions in a water-rich 10) (a) W. Yao, X. Dou, Y. Lu, J. Am. Chem. Soc. 2015, 137, 54.
solvent in the presence of a newly developed morpholine- (b) X. Han, F. Zhong, Y. Wang, Y. Lu, Angew. Chem. Int. Ed. 2012, 51, 767.
derived chiral phase-transfer catalyst (B3970) without base 11) (a) Cinchona Alkaloids in Synthesis and Catalysis, ed. by C. E. Song, John
additives.16) Wiley and Sons, 2009.
(b) Privileged Chiral Ligands and Catalysts, ed. by Q.-L. Zhou, John Wiley and
Sons, 2011.
CF3 CF3 Ph

NO2
B3970 (1 mol%) (c) S. G. Hentges, K. B. Sharpless, J. Am. Chem. Soc. 1980, 102, 4263.
O + Ph
CF3 H2O/toluene (10:1), 0 °C, 2 h
CF3
OH
N
Boc 12) Y. Nakamoto, F. Urabe, K. Takahashi, J. Ishihara, S. Hatakeyama, Chem. Eur. J.
Br
N O 2013, 19, 12653.
Ph Ph
OH
Ph
13) U.-H. Dolling, O. Davis, E. J. J. Grabowski, J. Am. Chem. Soc. 1984, 106, 446.
CF3 NO2 1) Pd/C, H2 (1 atm), Ph
CF3

O
AcOEt/MeOH, 0 °C, 24 h
N 14) T. Hashimoto, K. Maruoka, Chem. Rev. 2007, 107, 5656.
2) TFA, CH2Cl2, rt, 0.5 h
CF3 CF3 N N
Boc 3) LiAlH4, THF, 75 °C, 2 h
H 15) T. Ooi, M. Kameda, K. Maruoka, J. Am. Chem. Soc. 1999, 121, 6519.
B3970
Y. 93% (dr = 93 : 7, 90% ee) (90% ee)
16) R. He, S. Shirakawa, K. Maruoka, J. Am. Chem. Soc. 2009, 131, 16620.
17) D. Enders, O. Niemeier, A. Henseler, Chem. Rev. 2007, 107, 5606.
Nucleophilic carbene is an emerging class of asymmetric 18) (a) M. He, J. R. Struble, J. W. Bode, J. Am. Chem. Soc. 2006, 128, 8418.
organocatalysis. Since the report of the first asymmetric (b) M. He, G. J. Uc, J. W. Bode, J. Am. Chem. Soc. 2006, 128, 15088.
intramolecular Stetter reaction by Enders et al., there have
been many reports on asymmetric carbon-carbon bond
formation reactions via umpolung of aldehydes mediated by
N-heterocyclic carbene (NHC) catalysts.17) Bode et al. have
reported highly enantioselective Diels–Alder reactions to afford
dihydropyridinones using an NHC catalyst (D3983) generated
in situ.18)

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Asymmetric Organocatalysts

P0481 25g 250g P0994 5g 25g F0818 50mg

Prolines and
F

OH OH OH

Their Analogs N
H
O
N
H
O
N
H
O

trans-4-Fluoro- L-proline
L-Proline [147-85-3] D -Proline [344-25-2] [2507-61-1]
M2077 1g 5g B3440 1g 5g I0589 1g I0395 1g 5g O0370 1g 5g

H3C H
H3C C Si O
CH3 O
H3C O
OH OH OH
N N C OH N N N C OH
H H H H H H
O O O
trans-4-(tert-Butyl- (2S,3aS,7aS)-Octahydro-
α-Methyl- L-proline diphenylsilyloxy)- L-proline (R)-(+)-Indoline-2-carboxylic (S)-(-)-Indoline-2-carboxylic 1H-indole-2-carboxylic
[42856-71-3] [259212-61-8] Acid [98167-06-7] Acid [79815-20-6] Acid [80875-98-5]
P1382 1g 5g 25g P2083 1g 5g T3080 100mg H1407 200mg 1g A2206 200mg

O O H OH
O N
O N
N C NH S H
N C NH2 N C NH2 H S O N CH2NH2
H H O H
CH3
N-(2-Thiophenesulfonyl)- CH3
L-prolinamide Singh's Catalyst (S)-2-(Aminomethyl)-
L-Prolinamide [7531-52-4] D -Prolinamide [62937-45-5] [1089663-51-3] [910110-45-1] pyrrolidine [69500-64-7]
A1301 1g 5g A0945 1g 5g P1925 1g P1241 1g 5g M1183 1g 5g

N CH2 N
N CH2NH2 N CH2NH N CH2 N N CH2 N CH3
H H H
CH2CH3
(R)-(-)-1-(2-Pyrrolidinyl- (S)-(+)-1-(2-Pyrrolidinyl- (S)-(-)-1-Methyl-
(S)-(-)-2-Aminomethyl-1-ethyl- (S)-(+)-2-(Anilinomethyl)- methyl)pyrrolidine methyl)pyrrolidine 2-(1-piperidinomethyl)-
pyrrolidine [22795-99-9] pyrrolidine [64030-44-0] [60419-23-0] [51207-66-0] pyrrolidine [84466-85-3]
M1169 1g 5g M1161 1g 5g D2365 1g 5g D2735 1g 5g H0784 1g 5g
OH OH OH
N C N C N C
H H
CH3

N CH2OCH3 N CH2OCH3
H H
(R)-(+)-α,α-Diphenyl- (S)-(-)-α,α-Diphenyl- (R)-(-)-2-[Hydroxy(diphenyl)-
(R)-2-(Methoxymethyl)- (S)-2-(Methoxymethyl)- 2-pyrrolidinemethanol 2-pyrrolidinemethanol methyl]-1-methylpyrrolidine
pyrrolidine [84025-81-0] pyrrolidine [63126-47-6] [22348-32-9] [112068-01-6] [144119-12-0]
H0768 100mg 1g 5g D3804 1g D3185 100mg D3186 100mg P1784 100mg 500mg
OH
N C
N N
N
CH3 H N N
H N N N
H H H

(S)-(+)-2-[Hydroxy(diphenyl)-
methyl]-1-methylpyrrolidine
[110529-22-1]
A1043 100mg 1g
O
OH
NH
L-Azetidine-2-carboxylic
Acid [2133-34-8]
(S)-(-)-2-(Diphenylmethyl)- (2R,5R)-2,5-Diphenyl- (2S,5S)-2,5-Diphenyl- (S)-5-(Pyrrolidin-2-yl)-
pyrrolidine [119237-64-8] pyrrolidine [155155-73-0] pyrrolidine [295328-85-7] 1H-tetrazole [33878-70-5]
P1830 5g 25g P1404 1g 5g T0219 25g 500g M1995 1g
O
HO C
NH N
N
O O CH3
N C OH N C OH
S . 2HCl
H H
(S)-2-[(1-Methyl-
2-pyrrolidinyl)methyl]-
D -Pipecolic Acid [1723-00-8] L-Pipecolic Acid [3105-95-1] L-Thioproline [34592-47-7] isoindoline Dihydrochloride
A0179 25g 250g A0177 5g 25g M0099 25g 100g 500g

O O O

Amino Acids CH3

OH
CH3
OH
CH3S
OH
NH2 NH2 NH2

L-Alanine [56-41-7] D -Alanine [338-69-2] L-Methionine [63-68-3]

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 Asymmetric Organocatalysts

M0102 5g 25g P0134 25g 250g P0135 5g 25g T0230 25g 100g 500g T0228 25g 100g 500g

O O O OH O OH O
CH3S
OH OH OH CH3 OH CH3 OH
NH2 NH2 NH2 NH2 NH2

D -Methionine [348-67-4] L-Phenylalanine [63-91-2] D -Phenylalanine [673-06-3] L-(-)-Threonine [72-19-5] D -(+)-Threonine [632-20-2]

B3398 1g 5g T0539 5g 25g T0541 25g 100g T2937 100mg

CH3 O Ph
CH3 O Si CH3
CH3
(CH3)3CO O O O CH3 N
Ph CH3
CH3
H
(CH3)3CO NH PPh2
CH3 OH OH OH
O
NH2 NH2 NH2
N N
H H O-TBDPS-D -Thr-N-Boc-
O-tert-Butyl- L-threonine L-tert-Leu-Diphenylphosphine
[4378-13-6] D -Tryptophan [153-94-6] L-Tryptophan [73-22-3] [1264520-63-9]
B1683 10g B1684 5g B1685 5g
CH2 CH H H
CH2 CH CH2 CH H
Cl
Cl
Cl
H N

Cinchona Alkaloids
N CH2 H N
HO HO HO
CH2 H CH2
CH3O CH3O

N N N
N-Benzylcinchonidinium N-Benzylquinidinium N-Benzylquininium
Chloride [69257-04-1] Chloride [77481-82-4] Chloride [67174-25-8]
B1689 5g C0347 25g C0348 25g C0349 25g C0350 25g 200g
H CH2 CH H CH2 CH H CH2 CH H H
CH2 CH CH2 CH
Cl

N H N H N H N N
CH2 HO HO HO
HO HO
H H
. 2HCl . 2H2SO4
. 2H2O
N N N N N
N-Benzylcinchoninium Cinchonidine Dihydrochloride Cinchonidine Sulfate
Chloride [69221-14-3] Cinchonidine [485-71-2] [24302-67-8] Dihydrate [524-61-8] Cinchonine [118-10-5]
C0351 25g C2728 100mg D4305 100mg D4306 100mg H0752 25g 250g
H CH2 CH2 CH2 H
CH2 CH CH3CH2
N
N N N N N
H H
N N H N
S N N
HO HO
H O O H
O O
. HCl CH3O
. HCl
. xH2O N

N N-[(9S)-8α-Cinchonan-9-yl]- N N N
Cinchonine Hydrochloride quinoline-8-sulfonamide N-(9-Deoxy-epi-cinchonin-9-yl)- N-(9-Deoxy-epi-cinchonidin-9-yl)- Hydroquinidine
Hydrate [5949-11-1] [1440939-88-7] picolinamide [1414851-55-0] picolinamide [1414851-57-2] Hydrochloride [1476-98-8]
E0974 100mg I0728 1g Q0006 5g 25g Q0010 5g 25g Q0028 25g 100g
CH3CH2 H H CH2 CH H
CH2CH3 CH2 CH CH2 CH
N N
N N H N
O O HO HO HO
H H H
N HO CH3O CH3O CH3O
. H2SO4
. 2H2O
OH N N 2
N N
α-Isocupreine β-Isocupreidine Quinidine Sulfate Dihydrate
[1476067-44-3] [253430-48-7] Quinidine [56-54-2] [6591-63-5] Quinine [130-95-0]
Q0030 25g Q0074 100mg 1g Q0076 100mg 1g
CH2 CH H

H CH2 CH CH2 CH
N
HO

CH3O . HCl N HOCH2 N

. 2H2O
CH2OH
N
Quinine Hydrochloride
Dihydrate [6119-47-7] Quincorine [207129-35-9] Quincoridine [207129-36-0]
B4138 200mg 1g
O CH3
N CH3

Chiral Imidazolidinones
CH2 C CH3
N
H CH3
(2S,5S)-(-)-2-tert-Butyl-3-
methyl-5-benzyl-
4-imidazolidinone
[346440-54-8]

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Asymmetric Organocatalysts

D2130 1g 5g D2131 1g 5g I0801 10mL

CH3
CH3

N O
B

Chiral Oxazaborolidines N
B
O
N
B
O

CH3 CH3 (S)-4-Isopropyl-3-(1-naphthyl-

(R)-5,5-Diphenyl-2-methyl-3,4- (S)-5,5-Diphenyl-2-methyl-3,4- methyl)-2,5,5-triphenyl-
propano-1,3,2-oxazaborolidine propano-1,3,2-oxazaborolidine 1,3,2-oxazaborolidine
[112022-83-0] [112022-81-8] [850661-66-4]
B3296 200mg 1g 5g B3549 1g D4808 50mg 200mg
CH3

N CH3
N N
Chiral Isothioureas S N S N
S N

(+)-BTM [885051-07-0] (-)-BTM [950194-37-3] HBTM-2.1 [1203507-02-1]

T1215 10g 25g

N S

. HCl
(-)-Tetramisole Hydrochloride
[16595-80-5]
B1100 5g 25g B1142 5g 25g D2730 1g 5g
Br

OH OH OH
Chiral Diols OH OH OH

Br
(S)-(-)-1,1'-Bi-2-naphthol (R)-(+)-1,1'-Bi-2-naphthol (S)-(+)-6,6'-Dibromo-1,1'-bi-
[18531-99-2] [18531-94-7] 2-naphthol [80655-81-8]
D2729 1g D2811 1g 5g D2810 1g 5g O0283 1g 5g O0282 1g 5g 25g
Br Br Br

OH OH OH OH OH
OH OH OH OH OH

Br Br Br
(R)-(-)-6,6'-Dibromo-1,1'-bi- (S)-3,3'-Dibromo-1,1'-bi- (R)-3,3'-Dibromo-1,1'-bi- (S)-(-)-5,5',6,6',7,7',8,8'-Octahydro- (R)-(+)-5,5',6,6',7,7',8,8'-Octahydro-
2-naphthol [65283-60-5] 2-naphthol [119707-74-3] 2-naphthol [111795-43-8] 1,1'-bi-2-naphthol [65355-00-2] 1,1'-bi-2-naphthol [65355-14-8]
D5107 1g D4418 1g 5g B1615 1g B1614 1g 5g B2048 1g 5g
Br Br
OH HO
OH HO OH HO
OH OH
O O
OH OH
H3C O O O O

H3C CH3 H3C CH3

Br
(S)-(-)-3,3'-Dibromo-
5,5',6,6',7,7',8,8'-octahydro-1,1'-
bi-2-naphthol [765278-73-7]
Br
(R)-(+)-3,3'-Dibromo-
5,5',6,6',7,7',8,8'-octahydro-1,1'-bi-
2-naphthol [65355-08-0]
(+)-4,5-Bis[hydroxy(diphenyl)- (-)-4,5-Bis[hydroxy(diphenyl)- (+)-4,5-Bis[hydroxy(diphenyl)-
methyl]-2-methyl-2-phenyl- methyl]-2,2-dimethyl- methyl]-2,2-dimethyl-
1,3-dioxolane [109306-21-0] 1,3-dioxolane [93379-48-7] 1,3-dioxolane [93379-49-8]
M2765 50mg B1143 100mg 1g 5g
O O
CH3O S
N
O
N O

Chiral Phosphoric Acids

O P OH
O
P OH
O
O

(S)-3-[1-(4-Methoxybenzenesulfonyl)-(4S,5S)-4,5-diphenyl- (R)-(-)-1,1'-Binaphthyl-
4,5-dihydro-1H-imidazol-2-yl]-1,1'-binaphthalene- 2,2'-diyl Hydrogen
2,2'-diyl Hydrogen Phosphate [1621994-95-3] Phosphate [39648-67-4]
B1144 100mg 1g

O
O
P OH
O

(S)-(+)-1,1'-Binaphthyl-
2,2'-diyl Hydrogen
Phosphate [35193-64-7]

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 Asymmetric Organocatalysts

C0015 25g 100g 500g C0972 25g 100g 500g D4445 100mg

CH3 CH3 SO3K

CH3 CH3

Chiral Sulfonic Acids O

CH2SO3H HO3SCH2
O
SO3K

Dipotassium (R)-1,1'-
(+)-10-Camphorsulfonic (-)-10-Camphorsulfonic Binaphthyl-2,2'-disulfonate
Acid [3144-16-9] Acid [35963-20-3] [1092934-19-4]
D4663 20mg E1267 50mg
H C(CH3)3
N CF3
S
O O
C(CH3)3
NH

Chiral Amines
NH2
CO2CH2CH3
C(CH3)3

N-[(11bS)-4,5-Dihydro-
3H-dinaphtho[2,1-c:1',2'-e]- C(CH3)3

azepin-2-yl]trifluoromethane- Ethyl (11bR)-4-Amino-2,6-bis(3,5-di-tert-butylphenyl)-4,5-dihydro-3H-

sulfonamide [871915-77-4] cyclohepta[1,2-a:7,6-a']dinaphthalene-4-carboxylate [1678540-23-2]
P2380 50mg
(CH3)3C C(CH3)3

OH

N N

OH

(CH3)3C C(CH3)3

(S)-[4-(Pyridin-4-yl)-4,5-dihydro-3H-dinaphtho[2,1-c:1',2'-e]azepine-
2,6-diyl]bis[bis[4-(tert-butyl)phenyl]methanol] [1883396-49-3]
B3970 50mg D3475 200mg 1g
CF3 CF3

CF3 CF3 CH3

OH
Br CH2Ph
O CH2 N CH2 CH3

Chiral Ammonium Salts

N O 2

OH
CF3 CF3 O CH2 N CH2 CH3
CH2Ph 2
CF3 CF3 CH3
2BF4
(11bS)-2,6-Bis[bis[3,5-bis(trifluoromethyl)phenyl]-
hydroxymethyl]-3,5-dihydrospiro[4H-dinaphth[2,1-c:1',2'-e]-
azepine-4,4'-morpholinium] Bromide [1197922-04-5] (R,R)-TaDiAS-2nd
D3476 200mg 1g

CH3
CH2Ph
O CH2 N CH2 CH3
2

O CH2 N CH2 CH3

CH2Ph 2
CH3
2BF4

(S,S)-TaDiAS-2nd
D3984 100mg D3983 100mg
CH3 CH3 CH3 CH3

Chiral N-Heterocyclic H
N
N
N CH3
H
N
N
N CH3

Carbenes (NHC) H
O
Cl
. H2O H
O
Cl
. H2O
Bode Catalyst 1 Bode Catalyst 2
Monohydrate [919102-70-8] Monohydrate [903571-02-8]

B3592 200mg 1g B3593 200mg 1g

BF4 BF4

N N
N CF3 N CF3
N N

(R)-Benzyl-2-[4-(trifluoromethyl)phenyl]-6,7-dihydro- (S)-Benzyl-2-[4-(trifluoromethyl)phenyl]-6,7-dihydro-
5H-pyrrolo[2,1-c][1,2,4]triazolium Tetrafluoroborate [862095-77-0] 5H-pyrrolo[2,1-c][1,2,4]triazolium Tetrafluoroborate
I0807 200mg L0137 5mL 25mL L0236 1g 5g

Others
CH3 CH3 CH3 CH3
O I O
O O CH3 CH3
N N OH OH
CH3 H CH3 CH3 H CH3
CH3 NH2 CH3 NH2
(R,R)-2-Iodo-1,3-bis[1-(mesityl-
carbamoyl)ethoxy]benzene
[1226896-38-3] L-(+)-Leucinol [7533-40-6] D -(-)-Leucinol [53448-09-2]

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