Electron deficient dienes .1. Normal and inverse electron demand Diels-Alder reactions of the same carbon skeleton.

被引：36

作者：

Bodwell, GJ

Pi, ZL

机构：

[1] Department of Chemistry, Memorial University of Newfoundland, St John's, NF

来源：

TETRAHEDRON LETTERS | 1997年 / 38卷 / 03期

基金：

加拿大自然科学与工程研究理事会;

关键词：

D O I：

10.1016/S0040-4039(96)02340-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis of compound 11, which features a diene moiety bearing electron withdrawing groups at the 1 and 3 positions, and its completely regioselective inverse electron demand Diels-Alder reactions with 1,1-diethoxyethylene, ethyl vinyl ether and styrene are described. Endo addition is preferred. The direct synthetic precursor of 11, in which one of the electron withdrawing groups (a ketone) is protected, participates in normal electron demand Diels-Alder reactions with 1,4-naphthoquinone and N-phenylmaleimide, but is unreactive towards 1,1-diethoxyethylene. Copyright (C) 1996 Elsevier Science Ltd

引用

页码：309 / 312

页数：4

共 40 条

[11] SYNTHESIS OF NOVEL CARBOPOLYCYCLES AND HETEROPOLYCYCLES .4. SYNTHESIS AND CYCLOADDITION REACTIONS OF HOMOADAMANTANO[4,5-C]CYCLOPENTADIENONES - A FACILE ROUTE TO [4,5]-FUSED HOMOADAMANTANOBENZENE DERIVATIVES [J].