(2S,3S,8aR)-2-Phenyl-3-hydroxymethyl-8a-methyl bicyclic lactam

Preparation

The chiral bicyclic lactams are easily procured via condensation of commercially available  (1S,2S)-(+)-2-amino-1-phenyl-1,3-propanediol and the appropriate δ-keto acid (eq 1). Similar bicyclic lactams  have been prepared from other amino alcohols and have been extensively utilized in the stereocontrolled  formation of quaternary carbon-carbon bonds.