Reaction of cyclic alpha-hydroxy epoxides with a strong base: A new 1,2-rearrangement, evidence for a carbenoid pathway

被引：31

作者：

Doris, E

Dechoux, L

Mioskowski, C

机构：

[1] UNIV STRASBOURG 1,LAB SYNTHESE BIOORGAN,FAC PHARM,CNRS,F-67401 ILLKIRCH GRAFFENS,FRANCE

[2] CEA SACLAY,CE SACLAY,DEPT BIOL CELLULAIRE & MOLEC,SERV MOLEC MARQUEES,F-91191 GIF SUR YVETTE,FRANCE

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 1995年 / 117卷 / 51期

关键词：

D O I：

10.1021/ja00156a006

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Several substituted five- and six-membered cyclic alpha,beta-unsaturated ketones are readily available by treatment of the corresponding alpha-hydroxy epoxides with an organolithium reagent. The reaction involves a new carbenoid 1,2-alkyl rearrangement. Evidence for the carbenoid intermediate has been obtained by an intramolecular trapping of the highly reactive species.

引用

页码：12700 / 12704

页数：5

共 31 条

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