Highly regioselective nucleophilic substitution of cyclic carbonates of threo-2,3-dihydroxy esters: synthesis of optically pure β-hydroxy esters

Abstract

The nucleophilic ring opening of the cyclic carbonates of optically active threo-2,3-dihydroxy esters 1 afforded the α-substituted β-hydroxy esters 2 with highly regio- and stereo-selectivity under mild conditions. The α-sulfanyl or α-iodo β-hydroxy esters 2 thus obtained were transformed to the β-hydroxy esters 3, which are useful chiral synthons for natural product synthesis.