Tetrahedron letters

Regioncontrolled formation of iodohy dnns and expoxides from Vic-diols

M Adiyaman, SP Khanapure, SW Hwang, J Rokach

文献索引：Adiyaman; Khanapure; Hwang; Rokach Tetrahedron Letters, 1995 , vol. 36, # 41 p. 7367 - 7370

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被引用次数: 23

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 ...