Organocatalytic direct Michael reaction of ketones and aldehydes with β-nitrostyrene in brine

被引：436

作者：

Mase, N

Watanabe, K

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 / 15期

关键词：

D O I：

10.1021/ja060338e

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

We have developed a direct, asymmetric Michael reaction that can be performed in brine or seawater without addition of organic solvents. A bifunctional catalyst with long hydrophobic alkyl chains efficiently catalyzed Michael reactions and afforded the desired products in excellent yield with high enantiomeric excess, even when only an equal molar ratio of the donor to acceptor was used. Copyright © 2006 American Chemical Society.

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页码：4966 / 4967

页数：2

相关论文

共 22 条

[1]

ALEXAKIS A, 2002, SYNLETT, P26

[2] Catalytic direct asymmetric Michael reactions: Addition of unmodified ketone and aldehyde donors to alkylidene malonates and nitro olefins [J].

Betancort, JM ;

Sakthivel, K ;

Thayumanavan, R ;

Tanaka, F ;

Barbas, CF .

SYNTHESIS-STUTTGART, 2004, (09) :1509-1521

[3] Catalytic direct asymmetric Michael reactions: Taming naked aldehyde donors [J].

Betancort, JM ;

Barbas, CF .

ORGANIC LETTERS, 2001, 3 (23) :3737-3740

[4] Catalytic enantioselective direct Michael additions of ketones to alkylidene malonates [J].

Betancort, JM ;

Sakthivel, K ;

Thayumanavan, R ;

Barbas, CF .

TETRAHEDRON LETTERS, 2001, 42 (27) :4441-4444

[5] HYDROPHOBIC EFFECTS ON SIMPLE ORGANIC-REACTIONS IN WATER [J].

BRESLOW, R .

ACCOUNTS OF CHEMICAL RESEARCH, 1991, 24 (06) :159-164

[6] ANIONIC-INITIATED POLYMERIZATION OF BETA-NITROSTYRENES [J].

CARTER, ME ;

NASH, JL ;

DRUEKE, JW ;

SCHWIETERT, JW ;

BUTLER, GB .

JOURNAL OF POLYMER SCIENCE PART A-POLYMER CHEMISTRY, 1978, 16 (05) :937-959

[7] 5-Pyrrolidin-2-yltetrazole as an asymmetric organocatalyst for the addition of ketones to nitro-olefins [J].

Cobb, AJA ;

Longbottom, DA ;

Shaw, DM ;

Ley, SV .

CHEMICAL COMMUNICATIONS, 2004, (16) :1808-1809

[8] In the golden age of organocatalysis [J].

Dalko, PI ;

Moisan, L .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (39) :5138-5175

[9] Diphenylprolinol silyl ethers as efficient organocatalysts for the asymmetric Michael reaction of aldehydes and nitroalkenes [J].

Hayashi, Y ;

Gotoh, H ;

Hayashi, T ;

Shoji, M .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (27) :4212-4215

[10] A new class of chiral pyrrolidine-pyridine conjugate base catalysts for use in asymmetric Michael addition reactions [J].

Ishii, T ;

Fujioka, S ;

Sekiguchi, Y ;

Kotsuki, H .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (31) :9558-9559