Stereoselective Conjugate Addition of Organolithium and Organocopper Reagents to δ-Oxygenated α,β-Unsaturated Carbonyl Systems Derived from Glyceraldehyde Acetonide

Article abstract of DOI:10.1016/0040-4020(95)00875-9

Addition reactions of organolithium and organocopper reagents to δ-oxygenated α,β-unsaturated carbonyls, derived from glyceraldehyde acetonide, have been studied.In most cases there is a strong preference for conjugate addition of the organometallic reagent.Organocopper reagents react with anti stereoselectively, whereas most organolithium reagents react with syn stereoselectivity, except for phenyllithium which is unusual.