Chiral bicyclic lactams: useful precursors and templates for asymmetric syntheses1

Abstract

A survey of the utilitarian bicyclic lactams is presented. These chiral templates have provided, and continue to provide, access to a plethora of natural and unnatural carbocyclic products in high enantiomeric purity. Their synthetic versatility has recently grown with the development of new methods for the construction of heterocycles. In addition to the cyclopentenone, cyclohexenone and hexahydroindenone systems, products derived from bicyclic lactams now include optically active piperidines, pyrrolidines, pyrrolidinones and tetrahydroisoquinolines. These favourable properties make the bicyclic lactams highly adaptable tools for asymmetric synthesis.