Synthesis of γ-Lactams by Formal Cycloadditions with Ketenes
Audrey Viceriat, Isabelle Marchand, Sébastien Carret, Jean‐François Poisson
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.
Topics & Concepts
Enantiopure drugCycloadditionChemistryAziridineStereoselectivityFormal synthesisCombinatorial chemistryStereochemistryOrganic chemistryEnantioselective synthesisCatalysisRing (chemistry)Synthesis and Catalytic ReactionsSynthesis of β-Lactam CompoundsCatalytic C–H Functionalization Methods