Tetrahedron: Asymmetry

Novel synthesis of chiral, enantiomerically pure thiodiglycols and diglycols

J Christoffers, U Rößler

Index: Christoffers, Jens; Roessler, Ulrich Tetrahedron Asymmetry, 1998 , vol. 9, # 13 p. 2349 - 2357

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Citation Number: 18

Abstract

Natural α-hydroxy acids have been converted in a sequence of O-protection, reduction, O- activation, thioether and ether formation and deprotection to chiral, non-racemic β, β′- dihydroxy thioethers 1a, 1b and ether 1c. Overall yields are excellent (75%). In an attempt to synthesize the respective dihydroxy ether 1d derived from mandelic acid 1, 3-dioxolane derivatives 7 were obtained.