REGIOCONTROLLED FORMATION OF IODOHYDRINS AND EPOXIDES FROM VIC-DIOLS

被引：21

作者：

ADIYAMAN, M

KHANAPURE, SP

HWANG, SW

ROKACH, J

机构：

[1] FLORIDA INST TECHNOL,CLAUDE PEPPER INST,MELBOURNE,FL 32901

[2] FLORIDA INST TECHNOL,DEPT CHEM,MELBOURNE,FL 32901

来源：

TETRAHEDRON LETTERS | 1995年 / 36卷 / 41期

关键词：

D O I：

10.1016/0040-4039(95)01658-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel method for the stereoselective preparation of iodohydrins and epoxides from stereogenic vicinal diols is described. This new high-yield methodology consists of the conversion of thionocarbonates such as 12 to the primary iodo derivative 14 with complete regiocontrol. Deprotection of the secondary alcohol derivative in 14 gives the corresponding synthetically versatile iodohydrin 16, which is converted to epoxide 17. This methodology has been applied to complex tetraols 29 and 34. In the case of diols the transformation is conveniently carried out in high yield as a one-pot reaction.

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页码：7367 / 7370

页数：4

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