Catalysis Letters, Vol.145, No.2, 527-532, 2015
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
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.
Keywords:Morita-Baylis-Hillman reaction;Lipases;Aldol condensation;Enzymes in organic solvents;Enzyme promiscuity