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
收藏
页码：107 / 109
页数：3
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