PERICYCLIC UMPOLUNG - REVERSAL OF REGIOSELECTIVITY IN THE DIELS-ALDER REACTION

被引：43

作者：

SHEA, KJ

STAAB, AJ

ZANDI, KS

机构：

[1] Department of Chemistry University of California, Irvine, Irvine

来源：

TETRAHEDRON LETTERS | 1991年 / 32卷 / 24期

关键词：

D O I：

10.1016/0040-4039(91)85066-E

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

New methodology is reported which enables reversal of regiochemistry in the Diels-Alder reaction. Esterification of 2-(beta-hydroxyethyl)dimethylsilyldienes with common dienophiles followed by type 2 intramolecular Diels-Alder reaction results in formation of a single regio- and stereoisomer. Oxidative cleavage of the cycloadduct produces a cyclohexanone with a substitution pattern opposite of that found in the analogous bimolecular cycloaddition reaction.

引用

页码：2715 / 2718

页数：4

共 17 条

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