Catalytic asymmetric synthesis of β-hydroxy-α-amino acid esters by direct aldol reaction of glycinate Schiff bases

被引：45

作者：

Yoshikawa, N ^{[1
]}

Shibasaki, M ^{[1
]}

机构：

[1] Univ Tokyo, Grad Sch Pharmaceut Sci, Bunkyo Ku, Tokyo 1130033, Japan

来源：

TETRAHEDRON | 2002年 / 58卷 / 41期

基金：

日本学术振兴会;

关键词：

direct aldol reaction; heterobimetallic asymmetric catalyst; glycinate Schiff base; beta-hydroxy-alpha-amino acid; lanthanide; vancomycin; benzophenone imine; glycine;

D O I：

10.1016/S0040-4020(02)00979-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A catalytic asymmetric synthesis of beta-hydroxy-alpha-amino acid esters was developed using the direct aldol reaction of glycinate Schiff bases with aldehydes. The reaction was catalyzed by heterobimetallic asymmetric complexes without preformation of enol silyl ethers from glycinate Schiff bases. anti-beta-Hydroxy-alpha-amino acid esters were obtained as the major diastereomer in most cases, and moderate enantiomeric excess (up to 76% ee) was achieved for the first time for this type of reaction. Various substrates were also examined to investigate the effects of the protective groups for the amine or for the carboxylic acid moiety in glycine. (C) 2002 Elsevier Science Ltd. All rights reserved.

引用

页码：8289 / 8298

页数：10

共 80 条

[71]

SHIBASAKI M, 2000, LEWIS ACIDS ORGANIC, V2, pCH20

[72] Enantioselective synthesis of cis-2-oxazoline-4-carboxylates by Lewis acid catalyzed formal [3+2] cycloadditions of 5-alkoxyoxazoles with aldehydes [J].

Suga, H ;

Ikai, K ;

Ibata, T .

TETRAHEDRON LETTERS, 1998, 39 (08) :869-872

[73] Reversal of regioselection in the asymmetric aminohydroxylation of cinnamates [J].

Tao, B ;

Schlingloff, G ;

Sharpless, KB .

TETRAHEDRON LETTERS, 1998, 39 (17) :2507-2510

[74] DIASTEREOSELECTIVE ADDITION OF NUCLEOPHILES TO THE C3 POSITION OF N-(TOSYLOXY)-BETA-LACTAMS [J].

TENG, M ;

MILLER, MJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (02) :548-554

[75] Grignard reactions to chiral oxazolidine aldehydes [J].

Williams, L ;

Zhang, ZD ;

Shao, F ;

Carroll, PJ ;

Joullie, MM .

TETRAHEDRON, 1996, 52 (36) :11673-11694

[76] Direct catalytic asymmetric aldol reactions of aldehydes with unmodified ketones [J].

Yamada, YMA ;

Yoshikawa, N ;

Sasai, H ;

Shibasaki, M .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1997, 36 (17) :1871-1873

[77] Diastereo- and enantioselective direct catalytic aldol reaction of 2-hydroxyacetophenones with aldehydes promoted by a heteropolymetallic complex:: Catalytic asymmetric synthesis of anti-1,2-diols [J].

Yoshikawa, N ;

Suzuki, T ;

Shibasaki, M .

JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (08) :2556-2565

[78] Direct catalytic asymmetric aldol reaction:: Synthesis of either syn- or anti-α,β-dihydroxy ketones [J].

Yoshikawa, N ;

Kumagai, N ;

Matsunaga, S ;

Moll, G ;

Ohshima, T ;

Suzuki, T ;

Shibasaki, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (10) :2466-2467

[79] Direct catalytic asymmetric aldol reactions promoted by novel heterobimetallic catalysts possessing strong Bronsted base: a new strategy for the development of Lewis acid-Bronsted base bifunctional catalysts [J].

Yoshikawa, N ;

Shibasaki, M .

TETRAHEDRON, 2001, 57 (13) :2569-2579

[80] Direct catalytic asymmetric aldol reaction [J].

Yoshikawa, N ;

Yamada, YMA ;

Das, J ;

Sasai, H ;

Shibasaki, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (17) :4168-4178

← 1 2 3 4 5 6 7 8 →