PREPARATION OF SPIROCYCLIC CYCLOPROPYL KETONES THROUGH CONDENSATION OF EPOXIDES WITH BETA-KETO PHOSPHONATES

被引：28

作者：

JACKS, TE ^{[1
]}

NIBBE, H ^{[1
]}

WIEMER, DF ^{[1
]}

机构：

[1] UNIV IOWA,DEPT CHEM,IOWA CITY,IA 52242

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1993年 / 58卷 / 17期

关键词：

D O I：

10.1021/jo00069a018

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The beta-keto phosphonate derivatives of several cyclic ketones have been shown to undergo condensation with epoxides upon treatment with base, affording spirocyclic cyclopropyl ketones. Moderate to reasonable yields were obtained under sealed tube conditions with ethylene oxide, propylene oxide, and styrene oxide, and the substituted epoxides gave a single diastereomer in each case. The process can be viewed as an example of regiospecific geminal dialkylation, and cleavage of the cyclopropyl ring allows access to additional alpha,alpha-dialkylated ketones.

引用

页码：4584 / 4588

页数：5

共 38 条

[1] REGIOCHEMISTRY OF VINYL PHOSPHATE/BETA-KETO PHOSPHONATE REARRANGEMENTS IN FUNCTIONALIZED CYCLOHEXANONES AND DECALONES [J].