Bifunctional Organocatalysts for Enantioselective aza-Morita-Baylis-Hillman (aza-MBH) Reactions

Abstract

Powerful bifunctional organocatalysts, (S)-3-(N-isopropyl-N-3-pyridinylaminomethyl) BINOL (6a) and (S)-3-[2-(diphenylphosphino) phenyl] BINOL (10a), for the aza-Morita-Baylis-Hillman (aza- MBH) reaction, were developed. In these catalysts, chiral Bronsted acid units are connected with a Lewis base unit via a spacer. The acid-base moieties act cooperatively as an enzyme-mimetic catalyst to activate substrates in the carbon-carbon bond forming reaction between a, α, β-unsaturated carbonyl compounds and N-tosylimines with high enantioselectivity.