Kinetic Resolution in the Reaction of (2R,3R)-2,3-Diacetoxy- and (2R,3R)-2,3-Dibenzoyloxy-succinic Anhydrides with Racemic Alcohols

Abstract

The stereoselectivity in the reaction of various racemic alcohols with (2R,3R)-2,3-diacetoxy-and (2R,3R)-2,3-dibenzoyloxy-succinic anhydrides has been studied. Kinetic resolution values ranged up to 48%. A correlation between the absolute configuration of the more reactive enantiomeric alcohol with that of the chiral anhydride has been obtained. Attempted regeneration of the alcohols from the derived half-esters in the above reaction leads to partial racemization.