Hydrogen Bond Directed Nitrile Oxide Cycloaddition Reactions of Allylic 2°-Amides

Abstract

The ability of allylic and homoallylic 2°-amides to direct nitrile oxide cycloaddition reactions has been studied. For N-cyclopentenyl amides, good regio- and stereochemical control are observed and mechanistic studies suggest that hydrogen bonding in the transition state selectively accelerates formation of one isomer. Acyclic allylic and homoallylic 2°-amides do not exhibit high regio- or stereoselectivity