TANDEM ALKYNE INSERTION AND ALLYL SULFONIUM YLIDE REARRANGEMENT OF GAMMA,DELTA-ALKYNYL-ALPHA'-DIAZOKETONES

被引：24

作者：

HOYE, TR

DINSMORE, CJ

机构：

[1] Department of Chemistry University of Minnesota, Minneapolis

来源：

TETRAHEDRON LETTERS | 1992年 / 33卷 / 02期

关键词：

D O I：

10.1016/0040-4039(92)88041-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Acetylenic alpha-diazoketones 1, when treated with catalytic rhodium carboxylate dimer and diallylsulfide (1.1 equiv), undergo sequential alkyne insertion/ylide formation/sigmatropic rearrangement to give gamma-allylthio cyclic enones. This transformation was used to probe the influence of alkyne substituents on 5-exo vs. 6-endo cyclization selectivity in the alkyne insertion event.

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页码：169 / 172

页数：4

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