A novel chiral zirconium catalyst for enantioselective aldol and Mannich-type reactions. Catalytic activation of both aldehydes and imines using a similar chiral Lewis acid

被引：40

作者：

Kobayashi, S ^{[1
]}

Ishitani, H ^{[1
]}

Yamashita, Y ^{[1
]}

Ueno, M ^{[1
]}

Shimizu, H ^{[1
]}

机构：

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

来源：

TETRAHEDRON | 2001年 / 57卷 / 05期

关键词：

zirconium; aldehydes; imines; asymmetric catalysis;

D O I：

10.1016/S0040-4020(00)01038-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel zirconium catalyst has been developed for asymmetric aldol reaction of aldehydes with silyl enolates and asymmetric Mannich reactions of imines with silyl enolates. Similar types of catalysts have been successfully used in both reactions, and the desired products were obtained in high yields and high selectivities. For the sense of the chiral induction, reverse enantiofacial selectivities were observed between aldol reactions and Mannich reactions. (C) 2001 Elsevier Science Ltd. All rights reserved.

引用

页码：861 / 866

页数：6

共 61 条

[1]

AREND M, 1995, ANGEW CHEM, V107, P2861

[2] CATALYTIC ENANTIOSELECTIVE C-C COUPLING - ALLYL TRANSFER AND MUKAIYAMA ALDOL REACTION [J].

BACH, T .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1994, 33 (04) :417-419

[3]

BIORGO J, 1974, J CHEM SOC P2, P757

[4] STEREOSELECTIVE PREPARATION OF BETA-AMINO-ACYL IRON COMPLEXES FOR BETA-LACTAM SYNTHESIS [J].

BROADLEY, K ;

DAVIES, SG .

TETRAHEDRON LETTERS, 1984, 25 (16) :1743-1744

[5] CATALYTIC, ENANTIOSELECTIVE ALDOL ADDITIONS WITH METHYL AND ETHYL-ACETATE O-SILYL ENOLATES - A CHIRAL TRIDENTATE CHELATE AS A LIGAND FOR TITANIUM(IV) [J].

CARREIRA, EM ;

SINGER, RA ;

LEE, WS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (19) :8837-8838

[6]

CARREIRA EM, 1999, COMPREHENSIVE ASYMME, V3, P998

[7]

CHAN TH, 1991, COMPREHENSIVE ORGANI, V2

[8] HIGHLY ENANTIOSELECTIVE AND DIASTEREOSELECTIVE SYNTHESIS OF BETA-AMINO ACID-ESTERS AND BETA-LACTAMS FROM ACHIRAL ESTERS AND IMINES [J].

COREY, EJ ;

DECICCO, CP ;

NEWBOLD, RC .

TETRAHEDRON LETTERS, 1991, 32 (39) :5287-5290

[9] EXPEDIENT ROUTE TO 3-SUBSTITUTED AND 3,3'-SUBSTITUTED 1,1'-BI-2-NAPHTHOLS BY DIRECTED ORTHO METALATION AND SUZUKI CROSS COUPLING METHODS [J].

COX, PJ ;

WANG, W ;

SNIECKUS, V .

TETRAHEDRON LETTERS, 1992, 33 (17) :2253-2256

[10] Efficient regio- and enantioselective Mannich reactions [J].

Enders, D ;

Ward, D ;

Adam, J ;

Raabe, G .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1996, 35 (09) :981-984

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