Synthesis of optically active .beta.-lactams by the photolytic reaction of imines with optically active chromium carbene complexes

• Published in: Journal of the American Chemical Society Vol. 112; no. 3; pp. 1109 - 1117
• Main Authors: Hegedus, Louis S, Imwinkelried, Rene, Alarid-Sargent, Marie, Dvorak, Dalimil, Satoh, Yoshitaka
• Format: Journal Article
• Language: English
• Published: Washington, DC American Chemical Society 1990
• Subjects: Chemistry; Exact sciences and technology; Heterocyclic compounds; Heterocyclic compounds with only one n hetero atom and condensed derivatives; Organic chemistry; Preparations and properties; Carbene; Photolysis; Nitrogen heterocycle; Chromium Carbonyl Complexes; Lactam; Optical activity; Ketimine; Chiral compound; Transition metal Carbonyl Complexes; Diastereoselectivity; Aldimine; Oxygen nitrogen heterocycle
• ISSN: 0002-7863; 1520-5126
• DOI: 10.1021/ja00159a034

Optically active chromium carbene complexes utilizing (S)-valine- and (R)-phenylglycine-derived chiral auxillaries were synthesized and subjected to photolytic reaction with a number of imines. Optically active beta -lactams were produced in good to excellent chemical yield and with high diastereoisomeric excess. Procedures for removal of the chiral auxilliary to produce the optically active free amino beta -lactams were developed.