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

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 diastereois...

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Veröffentlicht in:	Journal of the American Chemical Society 1990, Vol.112 (3), p.1109-1117
Hauptverfasser:	Hegedus, Louis S, Imwinkelried, Rene, Alarid-Sargent, Marie, Dvorak, Dalimil, Satoh, Yoshitaka
Format:	Artikel
Sprache:	eng
Schlagworte:	Chemistry Exact sciences and technology Heterocyclic compounds Heterocyclic compounds with only one n hetero atom and condensed derivatives Organic chemistry Preparations and properties
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Zusammenfassung:	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.
ISSN:	0002-7863 1520-5126
DOI:	10.1021/ja00159a034