Stereoselective Preparation of Allylic Alcohol Intermediates in the Synthesis of Deoxysugars

Abstract

4S-cis-2,2,5-Trimethyl-l,3-dioxolane-4-carboxaldehyde(1) undergoes stereoselective nucleophilic addition with different vinyl metals. Allylic alcohols thus obtained are possible intermediates in the synthesis of deoxysugars. By a reiterative 1 C extension cycle, 6-deoxyhexoses can be obtained.