Promiscuous Lipase-Catalyzed C–C Bond Formation Reactions Between 4 Nitrobenzaldehyde and 2-Cyclohexen-1-one in Biphasic Medium: Aldol and Morita–Baylis–Hillman Adduct Formations

Abstract

Lipases catalyzed the reaction between 4-nitrobenzaldehyde and 2-cyclohexen-1-one in aqueous-DMSO co-solvent mixtures to give Morita–Baylis–Hillman product and aldol product. Among lipases, Burkholderia cepacia lipase gave the best overall conversion of 96 % in 50 % (v/v) DMSO while Mucor javanicus lipase showed highest stereoselectivity in the formation of the aldol (79 % ee) and Morita–Baylis–Hillman product (63 % ee) with 30 % (v/v) DMSO. Lipase catalysed Morita–Baylis–Hillman reaction