Catalytic enantioselective intermolecular reductive aldol reaction to ketones

被引：92

作者：

Zhao, DB ^{[1
]}

Oisaki, K ^{[1
]}

Kanai, M ^{[1
]}

Shibasaki, M ^{[1
]}

机构：

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

来源：

TETRAHEDRON LETTERS | 2006年 / 47卷 / 09期

基金：

日本学术振兴会;

关键词：

asymmetric catalysis; aldol reaction; ketones; copper fluoride; conjugate reduction; multi-component reaction;

D O I：

10.1016/j.tetlet.2005.12.097

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We describe the first example of a catalytic criantioselective intermolecular reductive aldol reaction. Three types of reactions were studied: (1) reactions between acetophenone and methyl acrylate; (2) reactions between symmetric ketones and beta-substituted a,p-unsaturated esters; and. (3) reactions between acetophenone derivatives and an allenic ester. Although only moderate enantioselectivity was obtained in the first reaction type, high to excellent enantioselectivity was realized in the enantio-induction at the alpha-position in the, second reaction type and at the delta-position in the third reaction type. Specifically, the third reaction type afforded the corresponding tertiary alcohols with up to 99% ee. Pre-activation of the nucleophile by silyl enolate formation is not necessary in these one-pot catalytic enantioselective reductive aldol reactions. (c) 2005 Elsevier Ltd. All rights reserved.

引用

页码：1403 / 1407

页数：5

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