Copper-Catalyzed ß-Lactam Formation Initiated by 1,3-Azaprotio Transfer of Oximes and Methyl Propiolate.

ABSTRACT

A copper(II)-catalyzed protocol to construct trans-configured ß-lactams and spirocyclic ß-lactams from oximes and methyl propiolate has been developed, which features excellent substrate flexibility and diastereoselectivity (up to >991 dr). In situ FT-IR mechanistic experiments support that ketene species might be involved in the formation of ß-lactams.