Synthesis of optically active alpha-methylene beta-lactams through lipase-catalyzed kinetic resolution.
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.
Adam
W
W
Institut für Organische Chemie and Institut für Lebensmittelchemie, Universität Würzburg, Am Hubland, D-97074 Würzburg, Germany. adam@chemie.uni-wuerzburg.de
Groer
P
P
Humpf
H U
HU
Saha-Möller
C R
CR
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*
D047090:beta-Lactams; D008049:Lipase