title: Synthesis of optically active alpha-methylene beta-lactams through lipase-catalyzed kinetic resolution.
abstract: A convenient method for the preparation of the hitherto unknown chiral alpha-methylene beta-lactam derivatives 5a,b is reported. The optically active alpha-methylene beta-lactams 5a-c, and their corresponding amino acids 6a-c have been readily made available through lipase-catalyzed kinetic resolution in high enantiomeric purity (up to 99% ee). The N-substituted beta-lactam derivatives 4a, b and 10 are not accepted by the lipases and were prepared in optically active form by chemical transformation.
authors.affiliation: Institut für Organische Chemie and Institut für Lebensmittelchemie, Universität Würzburg, Am Hubland, D-97074 Würzburg, Germany. adam@chemie.uni-wuerzburg.de
authors.forename: W
authors.initials: W
authors.lastname: Adam
authors.forename: P
authors.initials: P
authors.lastname: Groer
authors.forename: H U
authors.initials: HU
authors.lastname: Humpf
authors.forename: C R
authors.initials: CR
authors.lastname: Saha-Möller
mesh_terms: D002384:Catalysis; D002942:Circular Dichroism; D007700:Kinetics; D008049:Lipase / Q000378:metabolism*; D008745:Methylation; D008956:Models, Chemical; D013056:Spectrophotometry, Ultraviolet; D047090:beta-Lactams / Q000138:chemical synthesis*
chemical_list: D047090:beta-Lactams; D008049:Lipase