syn-Selective Michael Addition of Lithiated 2-Alkoxyacetates and -acetamides to α,β-Unsaturated Carbonyl Compounds

Abstract

Abstract The lithium Z-enolates derived from 2-alkoxyacetates and -acetamides undergo unusual syn-selective Michael addition to α,β-unsaturated carbonyl compounds, where the syn selectivity of the amide enolates is much higher than that of the ester enolates. Factors that influence the stereoselectivity are also discussed.