Stereoselective SN2′ alkylation reaction sequence of the γ,δ-epoxy α,β-unsaturated ester system via γ,δ-chlorohydrin intermediates by the use of a R3Al-CuCN reagent

被引：7

作者：

Yoshimura, Fumihiko ^{[1
]}

Matsui, Atsushi ^{[1
]}

Hirai, Atsushi ^{[1
]}

Tanino, Keiji ^{[1
]}

Miyashita, Masaaki ^{[1
]}

机构：

[1] Hokkaido Univ, Grad Sch Sci, Div Chem, Sapporo, Hokkaido 0600810, Japan

来源：

TETRAHEDRON LETTERS | 2009年 / 50卷 / 36期

关键词：

Epoxy unsaturated ester; S(N)2 ' alkylation reaction; Chlorohydrin; R3Al-CuCN reagent; Quaternary asymmetric carbon atom; STEREOSPECIFIC METHYLATION; ASYMMETRIC EPOXIDATION; POLYPROPIONATE CHAINS; TRIMETHYLALUMINUM; ACRYLATES;

D O I：

10.1016/j.tetlet.2009.06.106

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel stereoselective S(N)2' alkylation reaction sequence of the gamma,delta-epoxy alpha,beta-unsaturated ester system has been developed which involves a regioselective substitution reaction with chloride ions at the gamma-position and a Subsequent S(N)2' alkylation reaction of the resulting gamma-chloro-delta-hydroxy derivatives with a R3Al-CuCN reagent. The new methodology was demonstrated to be applicable to a variety of substrates and to provide various delta-hydroxy-alpha-alkyl-beta,gamma-unsaturated esters including those bearing a quaternary asymmetric carbon atom at the alpha-position in a highly stereoselective manner and high yields. (C) 2009 Elsevier Ltd. All rights reserved.

引用

页码：5126 / 5129

页数：4