Phosphine-catalyzed (3+3) annulation of cinnamaldehyde-derived Morita–Baylis–Hillman carbonates with dinucleophiles

Abstract

The phosphine-catalyzed (3+3) annulation reaction of cinnamaldehyde-derived Morita–Baylis–Hillman (MBH) carbonates with 1,3-dicarbonyl compounds as dinucleophiles has been developed, giving hexahydrochromenone derivatives in high yields with moderate to good diastereoselectivities. The reaction worked through double conjugate addition of 1,3-dicarbonyl compounds to the phosphonium intermediates generated from the cinnamaldehyde-derived MBH carbonates.