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
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.
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页码:12700 / 12704
页数:5
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