Highly Stereoselective Intermolecular Oxy-Michael Addition Reaction to α,β-Unsaturated Malonate Esters

Abstract

[reaction: see text] The highly diastereoselective oxy-Michael addition of the "naked" anion of (6S)-methyl delta lactol to alkylidiene-, arylidene-, and heteroarylidenemalonate derivatives leading to the direct formation of THP-protected beta-hydroxy ester derivatives is described. Subsequent acid-mediated deprotection affords the enantioenriched aldol products in quantitative yields.