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

Abstract
The highly diastereoselective oxy-Michael addition of the “naked” anion of (6S)-methyl δ lactol to alkylidiene-, arylidene-, and heteroarylidenemalonate derivatives leading to the direct formation of THP*-protected β-hydroxy ester derivatives is described. Subsequent acid-mediated deprotection affords the enantioenriched aldol products in quantitative yields.

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