Highly diastereoselective Michael reaction of (S)-mandelic acid enolate. Chiral benzoyl carbanion equivalent through an oxidative decarboxylation of α-hydroxyacids

Abstract

The reaction of the lithium enolate of the 1,3-dioxolan-4-one derived from optically active (S)-mandelic acid and pivalaldehyde with α,β-unsaturated carbonyl compounds proceeds readily to give the corresponding Michael adducts in good yields and high diastereoselectivity. Subsequent basic hydrolysis of the acetal and oxidative decarboxylation of the α-hydroxyacid moiety provides chiral 2-substituted 1,4-dicarbonyl compounds with very high enantiomeric excesses.