Phosphine-Catalyzed Asymmetric Intermolecular Cross-Vinylogous Rauhut–Currier Reactions of Vinyl Ketones with para-Quinone Methides

Abstract

A chiral amide-phosphine bifunctional catalyst was developed and successfully applied to the asymmetric intermolecular cross-vinylogous Rauhut–Currier of alkyl vinyl ketones with para-quinone methides, offering excellent regioselectivity and stereoselectivity (up to >99% enantiomeric excess (ee)). This method provides a facile access to structurally diverse widely existed diarylmethine stereogenic centers with excellent enantioselectivity. Density functional theory (DFT) calculations have been performed to understand the mechanism and enantioselectivity for this phosphine-catalyzed asymmetric transformation.