Organocatalyzed Synthesis of γ-Alkenyl Butenolides via Asymmetric Direct Vinylogous Conjugate Addition-Elimination of Substituted Furanone Derivatives to β-Phenylsulfonylenones.

A diaminomethylenemalononitrile organocatalyst efficiently promoted the asymmetric direct vinylogous conjugate addition of α-angelica lactone derivatives to β-phenylsulfonylenones, affording the corresponding γ-alkenyl γ-butenolides in high yields with excellent enantioselectivities (up to 97% ee) after the elimination of the phenylsulfonyl group. This study reports the first successful example of a stereoselective reaction using β-phenylsulfonylenone as the direct alkenyl donor.