Diastereoselectivity in the Carroll rearrangement of β-keto esters of tertiary allylic alcohols

被引：13

作者：

Jung, ME ^{[1
]}

Duclos, BA ^{[1
]}

机构：

[1] Univ Calif Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90095 USA

来源：

TETRAHEDRON LETTERS | 2004年 / 45卷 / 01期

基金：

美国国家卫生研究院;

关键词：

Carroll rearrangement; 3,3]-sigmatropic rearrangement; steric effects; electronic effects;

D O I：

10.1016/j.tetlet.2003.10.102

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Carroll rearrangement of beta-keto esters derived from tertiary allylic alcohols, for example, 7, under basic conditions followed by decarboxylation of the resulting beta-keto acids yielded the expected gamma,delta-unsaturated methyl ketones 8 with a range of olefin geometries from 100:0 to 1:1.8 E/Z, depending on the relative steric requirements of the two groups at the allylic center. (C) 2003 Elsevier Ltd. All rights reserved.

引用

页码：107 / 109

页数：3

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