Conjugate Addition of Reactive Carbanions to α,β-Unsaturated Ketones in the Presence of ATPH

Abstract

Aluminum tris(2,6-diphenylphenoxide) (ATPH) has been successfully utilized for effective blocking of carbonyl moieties, thereby allowing the conjugate addition of organolithium reagents to α,β-unsaturated ketones. In particular, conjugate addition of lithium alkynides and thermally unstable lithium carbenoids, which are very difficult to achieve in organocopper chemistry, are realized with α,β-unsaturated ketone/ATPH complexes.