Organocatalytic direct asymmetric aldol reactions in water

被引：648

作者：

Mase, N

Nakai, Y

Ohara, N

Yoda, H

Takabe, K

Tanaka, F

Barbas, CF

机构：

[1] Shizuoka Univ, Fac Engn, Dept Mol Sci, Hamamatsu, Shizuoka 4328561, Japan

[2] Scripps Res Inst, Skaggs Inst Chem Biol, La Jolla, CA 92037 USA

[3] Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA

[4] Scripps Res Inst, Dept Mol Biol, La Jolla, CA 92037 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2006年 / 128卷 / 03期

关键词：

D O I：

10.1021/ja0573312

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

We have developed direct asymmetric cross-aldol reactions that can be performed in water without addition of organic solvents. A bifunctional catalyst with a long hydrophobic alkyl chain efficiently catalyzed the reactions and afforded the desired aldol products in excellent yield with high enantiomeric excess, even when only an equal molar ratio of the donor and acceptor was used. These results reveal an effective design strategy for the development of aqueous organocatalytic systems. Copyright © 2006 American Chemical Society.

引用

页码：734 / 735

页数：2

共 22 条

[1] Quantum mechanical predictions of the stereoselectivities of proline-catalyzed asymmetric intermolecular aldol reactions
Bahmanyar, S
Houk, KN
Martin, HJ
List, B
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (09) : 2475 - 2479
[2] Catalytic direct asymmetric Michael reactions: Addition of unmodified ketone and aldehyde donors to alkylidene malonates and nitro olefins
Betancort, JM
Sakthivel, K
Thayumanavan, R
Tanaka, F
Barbas, CF
[J]. SYNTHESIS-STUTTGART, 2004, (09): : 1509 - 1521
[3] HYDROPHOBIC EFFECTS ON SIMPLE ORGANIC-REACTIONS IN WATER
BRESLOW, R
[J]. ACCOUNTS OF CHEMICAL RESEARCH, 1991, 24 (06) : 159 - 164
[4] Protonated chiral prolinamide catalyzed enantioselective direct aldol reaction in water
Chimni, SS
Mahajan, D
Babu, VVS
[J]. TETRAHEDRON LETTERS, 2005, 46 (34) : 5617 - 5619
[5] Direct organocatalytic aldol reactions in buffered aqueous media
Córdova, A
Notz, W
Barbas, CF
[J]. CHEMICAL COMMUNICATIONS, 2002, (24) : 3024 - 3025
[6] Zn-proline catalyzed direct aldol reaction in aqueous media
Darbre, T
Machuqueiro, M
[J]. CHEMICAL COMMUNICATIONS, 2003, (09) : 1090 - 1091
[7] Observation of covalent intermediates in an enzyme mechanism at atomic resolution
Heine, A
DeSantis, G
Luz, JG
Mitchell, M
Wong, CH
Wilson, IA
[J]. SCIENCE, 2001, 294 (5541) : 369 - 374
[8] Development of novel Lewis acid catalysts for selective organic reactions in aqueous media
Kobayashi, S
Manabe, K
[J]. ACCOUNTS OF CHEMICAL RESEARCH, 2002, 35 (04) : 209 - 217
[9] Stereoselective organic reactions in water
Lindström, UM
[J]. CHEMICAL REVIEWS, 2002, 102 (08) : 2751 - 2771
[10] Synthesis of β-hydroxyaldehydes with stereogenic quaternary carbon centers by direct organocatalytic asymmetric aldol reactions
Mase, N
Tanaka, F
Barbas, CF
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (18) : 2420 - 2423

← 1 2 3 →