The preparation of optically active 3-fluoro-β-lactam derivatives

✍ Scribed by J.T. Welch; R. Kawecki; J.A. Wichtowski; K. Araki

• Publisher: Elsevier Science
• Year: 1991
• Tongue: English
• Weight: 33 KB
• Volume: 54
• Category: Article
• ISSN: 0022-1139
• DOI: 10.1016/s0022-1139(00)83703-3

✦ Synopsis

Optically active 3-fluoro+lactam

(1) was stereoselectively synthesized by the ketene-imine condensation method. Use of (1) in alkylation and aldol reactions resulted in the stereoselective formation of ( 2) and ( 3) respectively, but the control of the hydroxylated stereocenter was not possible in the aldol reaction.

The selective reduction and alkylation of the ketone (4) prepared from the aldol products (3) will also be discussed. Additionally, the syntheses of other optically active 3-fluorinated p-lactams and a-fluorinated p-amino acids will be reported.