Asymmetric vinylogous Michael addition of 5-substituted-furan-2(3H)-ones to an α,β-unsaturated-γ-lactam.

Abstract

The manuscript describes an utilization of 5-substituted-furan-2(3H)-ones as pronucleophiles in an asymmetric vinylogous Michael addition to an α,β-unsaturated-γ-lactam, thus leading to hybrid molecules possessing γ-lactam and butenolide structural motifs. The transformation utilizes two potentially vinylogous pronucleophiles and has been realized by simultaneous activation of both substrates by a bifunctional organocatalyst derived from a cinchona alkaloid. Reaction occurs in a highly enantio- and diastereoselective manner and the synthetic potential of the target products has been confirmed in stereoselective transformations.