Squaramide-catalyzed aza-Michael/Michael cyclization cascade reaction: one-pot enantioselective construction of highly functionalized γ-lactams

Abstract

We report a squaramide-catalyzed aza-Michael/Michael cyclization of nitroalkenes with 3-benzoylacylamides, facilitating the asymmetric synthesis of γ-lactams. This method efficiently generates a range of optically pure γ-lactams, in yields ranging from 25% to 90% and enantioselectivities 71% to 99% under mild conditions. Moreover, this reaction demonstrates exceptional compatibility with a variety of functional groups and offers a wide array of subsequent transformation possibilities.