Cooperative Isothiourea/Iridium-Catalyzed Asymmetric Annulation Reactions of Vinyl Aziridines with Pentafluorophenyl Esters

Abstract

Chiral γ-lactam-containing skeletons are important motifs in bioactive natural products, pharmaceuticals, and bioactive molecules. Herein, we report a general and modular platform to access chiral γ-lactam compounds via an ITU/Ir cooperatively catalyzed [3 + 2] asymmetric annulation reaction of vinyl aziridines with pentafluorophenyl esters. Through the Lewis base and transition metal cooperative catalytic regime, a broad range of optically active γ-lactams were generated in good yields (up to 92%) with high asymmetric induction (up to 98% ee). Furthermore, the utility of this synthetic protocol was also demonstrated by the expedient preparation of diverse enantioenriched architectures.

Topics & Concepts