One-pot synthesis of functionalized dihydropyridin-2-ones via carbene-catalyzed base-controlled [3+3] annulation reaction

Abstract

Herein, we have described a novel organocatalytic approach to access biologically important dihydropyridin-2-ones in a one-pot way with generally high yields (up to 99%) and excellent enantioselectivities (up to 99% ee). This reaction proceeded via a new dual activation mode, including in situ-generated α,β-unsaturated acylazoliums and 4-dimethylaminopyridinium salts that underwent a Michael addition/1,4-H migration/lactamization sequence. The base-triggered 4-dimethylaminopyridinium ylide formation pathway over the competing substitution reaction pathway of vicinal haloamines is noteworthy.