Dibutyltin dimethoxide and BINAP•silver(I) complex-catalyzed asymmetric aldol reaction of alkenyl trichloro acetates with aldehydes

被引：10

作者：

Yanagisawa, Akira ^{[1
]}

Ichikawa, Toshikazu

Arai, Takayoshi

机构：

[1] Chiba Univ, Fac Sci, Dept Chem, Inage Ku, Chiba 2638522, Japan

[2] Chiba Univ, Grad Sch Sci & Technol, Inage Ku, Chiba 2638522, Japan

来源：

JOURNAL OF ORGANOMETALLIC CHEMISTRY | 2007年 / 692卷 / 1-3期

关键词：

asymmetric catalysis; aldol reaction; tin alkoxide-1; BINAP; silver; alkenyl esters; aldehydes;

D O I：

10.1016/j.jorganchem.2006.08.048

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

A catalytic asymmetric aldol reaction of alkenyl trichloroacetates with aldehydes was achieved using dibutyltin dimethoxide and BINAP (.) silver(I) complex as catalysts in a mixed solvent consisting of THF and MeOH. Various optically active beta-hydroxy ketones were diastereoselectively obtained not only from aromatic and alpha,beta-unsaturated aldehydes but also from an aliphatic aldehyde with good enantioselectivity up to 92% ee. (c) 2006 Elsevier B.V. All rights reserved.

引用

页码：550 / 553

页数：4

共 46 条

[1] The direct catalytic asymmetric cross-aldol reaction of aldehydes [J].

Alcaide, B ;

Almendros, P .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (08) :858-860

[2]

[Anonymous], 2004, MODERN ALDOL REACTIO

[3]

[Anonymous], 2004, MODERN ALDOL REACTIO

[4] Advances in asymmetric enolate methodology [J].

Arya, P ;

Qin, HP .

TETRAHEDRON, 2000, 56 (07) :917-947

[5] 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

[6]

BRAUN M, 1995, HOUBENWEYL METHODS E, V21, P1603

[7]

BRAUN M, 1995, HOUBENWEYL METHODS E, V21, P1730

[8]

Carreira E. M., 2000, MODERN CARBONYL CHEM, P227

[9]

CARREIRA EM, 1999, COMPREHENSIVE ASYMME, V3, P997

[10] Chemistry of trichlorosilyl enolates .1. New reagents for catalytic, asymmetric aldol additions [J].

Denmark, SE ;

Winter, SBD ;

Su, XP ;

Wong, KT .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (31) :7404-7405

← 1 2 3 4 5 →