Organocatalytic asymmetric 1,4-addition of organoboronic acids to γ-hydroxy α,β-unsaturated aldehyde:: facile synthesis of chiral β-substituted γ-lactones

被引：31

作者：

Kim, Sung-Gon ^{[1
]}

机构：

[1] Kyonggi Univ, Dept Chem, Coll Nat Sci, Suwon 443760, South Korea

来源：

TETRAHEDRON LETTERS | 2008年 / 49卷 / 42期

关键词：

organocatalyst; asymmetric 1,4-addition; organoboronic acid; gamma-lactol; gamma-lactone;

D O I：

10.1016/j.tetlet.2008.08.025

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Catalytic asymmetric 1,4-addition of arylvinyl- and arylboronic acids to a gamma-hydroxy alpha,beta-unsaturated aldehyde, which affords beta-substituted gamma-lactols, has been established using a diarylprolinol silyl ether as an organocatalyst. The beta-substituted gamma-lactols have been obtained in good yields and with up to 91% ee, which lead to chiral beta-substituted gamma-lactones followed by oxidation. (c) 2008 Elsevier Ltd. All rights reserved.

引用

页码：6148 / 6151

页数：4

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