Tetrahedron

Stereoselective synthesis of enantiopure 4, 5-dihydroxy-2-alkene esters from simple allylic alcohols

MPM van Aar, L Thijs, B Zwanenburg

Index: Aar, Marcel P. M. van; Thijs, Lambertus; Zwanenburg, Binne Tetrahedron, 1995 , vol. 51, # 35 p. 9699 - 9712

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Citation Number: 3

Abstract

A general stereoselective synthesis of 4.5-dihydroxy-2-alkene esters is developed using the photo-induced rearrangement of α, β-epoxy diazomethyl ketones. Starting with readily available enantiopure allylic alcohols that contain a chiral center at C4, ie a protected secondary alcohol function, a neighboring stereogenic center is introduced by irradiation of the mentioned diazo ketones. The configuration of this newly introduced center is ...

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