Convenient enantioselective synthesis of β-trifluoromethyl-β-aminoketones by organocatalytic asymmetric Mannich reaction of aryl trifluoromethyl ketimines with acetone

被引：81

作者：

Sukach, Volodymyr A. ^{[1
]}

Golovach, Nataliya M. ^{[1
]}

Pirozhenko, Volodymyr V. ^{[1
]}

Rusanov, Eduard B. ^{[1
]}

Vovk, Mykhaylo V. ^{[1
]}

机构：

[1] Natl Acad Sci Ukraine, Inst Organ Chem, UA-02094 Kiev, Ukraine

来源：

TETRAHEDRON-ASYMMETRY | 2008年 / 19卷 / 06期

关键词：

D O I：

10.1016/j.tetasy.2008.02.023

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The L-proline-catalyzed asymmetric Mannich reaction has been performed between aryl trifluoromethyl ketimines and acetone to provide, for the first time, chiral beta-aryl-beta-trifluoromethyl-beta-aminoketones in high yields and with 74-92% enantiomeric excesses. (c) 2008 Elsevier Ltd. All rights reserved.

引用

页码：761 / 764

页数：4

共 47 条

[1] Arend M, 1998, ANGEW CHEM INT EDIT, V37, P1044, DOI 10.1002/(SICI)1521-3773(19980504)37:8<1044::AID-ANIE1044>3.0.CO
[2] 2-E
[3] Origins of opposite absolute stereloselectivities in proline-catalyzed direct Mannich and aldol reactions
Bahmanyar, S
Houk, KN
[J]. ORGANIC LETTERS, 2003, 5 (08) : 1249 - 1251
[4] Reactivity of stable trifluoroacetaldehyde hemiaminals. I. An unexpected reaction with enolizable carbonyl compounds
Blond, G
Billard, T
Langlois, BR
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (14) : 4826 - 4830
[5] Unexpected and expeditious entry into trifluoromethyl aziridines from substituted β-dicarbonyl compounds
Colantoni, D
Fioravanti, S
Pellacani, L
Tardella, PA
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (23) : 9648 - 9650
[6] The direct catalytic asymmetric Mannich reaction
Córdova, A
[J]. ACCOUNTS OF CHEMICAL RESEARCH, 2004, 37 (02) : 102 - 112
[7] MULTIFUNCTIONAL BIS-(TRIFLUOROMETHYL) SUBSTITUTED SYNTHETIC INTERMEDIATES FROM 4,4-BIS-(TRIFLUOROMETHYL)-1-OXA-3-AZABUTA-1,3-DIENES VIA BAYLIS-HILLMAN REACTION
CYRENER, J
BURGER, K
[J]. MONATSHEFTE FUR CHEMIE, 1994, 125 (11): : 1279 - 1285
[8] Dimmock JR, 2004, PHARMAZIE, V59, P502
[9] Elucidation of solvent exposure, side-chain reactivity, and steric demands of the trifluoromethionine residue in a recombinant protein
Duewel, HS
Daub, E
Robinson, V
Honek, JF
[J]. BIOCHEMISTRY, 2001, 40 (44) : 13167 - 13176
[10] FETYUKHIN VN, 1977, J ORG CHEM USSR, V13, P244

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