Synthesis of γ-Lactams by Formal Cycloadditions with Ketenes

Org Lett. 2021 Apr 2;23(7):2449-2454. doi: 10.1021/acs.orglett.1c00335. Epub 2021 Mar 11.

Abstract

The synthesis of γ-lactams is reported by a formal (3+2) cycloaddition between readily available ketenes and aziridines or a one-pot formal (2+1+2) cycloaddition using imines as aziridine precursors. The method is practical, is scalable, and affords high yields. It also offers a high level of regio- and diastereoselectivity on a wide range of substrates as well as a high stereoselectivity in the case of enantiopure aziridines.

Publication types

  • Research Support, Non-U.S. Gov't