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 ȧ reiterative 1 C extension cycle, 6-deoxyhexoses can be obtained.