Chiral quaternary alkylammonium ionic liquid [Pro-dabco][BF 4]: as a recyclable and highly efficient organocatalyst for asymmetric Michael addition reactions

Abstract

A novel series of chiral quaternary ammonium ionic liquids have been synthesized and shown to be very effective catalysts for the asymmetric Michael addition reactions of ketones and aldehydes to nitroolefins with excellent yields (up to 100%), diastereoselectivities ( syn/ anti = 99:1), and enantioselectivities (up to 97%). The catalytic system, an ionic liquid organocatalyst in [Bmim][BF 4], could be reused five times without a significant loss in catalytic activity or stereoselectivity.