REACTION OF EPOXIDES WITH ACTIVATED DMSO REAGENT - GENERAL-METHOD FOR SYNTHESIS OF ALPHA-CHLOROCARBONYL COMPOUNDS - APPLICATION IN ASYMMETRIC-SYNTHESIS OF (3S)-2,3-OXIDOSQUALENE

被引：18

作者：

RAINA, S ^{[1
]}

SINGH, VK ^{[1
]}

机构：

[1] INDIAN INST TECHNOL,DEPT CHEM,KANPUR 208016,UTTAR PRADESH,INDIA

来源：

TETRAHEDRON | 1995年 / 51卷 / 08期

关键词：

D O I：

10.1016/0040-4020(94)01111-C

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Reaction of a variety of epoxides with DMSO-Oxalyl chloride in the presence of a catalytic amount of methanol and a base was studied. Disubstituted epoxides gave alpha-chloroketones in high yields. Aliphatic terminal epoxide underwent opening reaction to provide alpha-chloroketone as a major product. Trisubstututed epoxides provided alpha-chloroketones as major products through the formation of more stable carbocation. In case of a homoallylic alcohol, enedione was obtained. The efficiency of the method was shown by applying it to the enantioselective synthesis of (3S)-2,3-oxidosqualene.

引用

页码：2467 / 2476

页数：10

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