Catalytic Enantioselective Synthesis of β‐Lactams: Intramolecular Kinugasa Reactions and Interception of an Intermediate in the Reaction Cascade

Abstract

A planar-chiral Cu/phosphaferrocene–oxazoline catalyst mediates intramolecular Kinugasa reactions to give tricyclic β-lactams with good enantioselectivity. A variant of the process, in which a postulated enolate intermediate is intercepted with an electrophile in a transformation that generates two CC bonds, a CN bond, two new rings, a carbonyl group, and adjacent tertiary and quaternary stereocenters (see scheme), supports the proposed mechanism. Supporting information for this article is available on the WWW under http://www.wiley-vch.de/contents/jc_2002/2003/z52103_s.pdf or from the author. Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article.