Stereoselective synthesis of functionalized butenolides by the photochemical rearrangement of [2,1]benzisoxazolequinone derivatives.

被引：2

作者：

Armesto, D ^{[1
]}

RodriguezMorgade, S ^{[1
]}

Ortiz, MJ ^{[1
]}

Vazquez, P ^{[1
]}

Torres, T ^{[1
]}

机构：

[1] UNIV AUTONOMA MADRID,DEPT QUIM ORGAN CI,E-28049 MADRID,SPAIN

来源：

TETRAHEDRON | 1997年 / 53卷 / 09期

关键词：

D O I：

10.1016/S0040-4020(97)00058-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

On direct irradiation 3-alkoxy[2,1]benzisoxazolequinones 1a, 1b, 1c, 1e and 3-N,N-dimethylamino[2,1]benzisoxazolequinone 1d undergo rearrangement to the corresponding gamma-cyano alkylidenebutenolides 3 in high yield. The reaction is highly stereoselective for compounds la, Ib, Ic, and Id yielding the corresponding Z-butenolides 3 as the only stereoisomer. A mechanism involving triplet nitrene intermediates is proposed for the reaction. (C) 1997 Elsevier Science Ltd.

引用

页码：3363 / 3368

页数：6

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