Lipase-catalyzed enantioselective ring opening of unactivated alicyclic-fused beta-lactams in an organic solvent.
[reaction: see text] A highly efficient and very simple method was developed for the synthesis of enantiopure beta-amino acids (e.g. cispentacin) and beta-lactams through the enzyme-catalyzed enantioselective ring opening of unactivated alicyclic beta-lactams in organic media. High enantioselectivity (E > 200) was observed when the Lipolase (lipase B from Candida antarctica)-catalyzed reactions were performed with H(2)O (1 equiv) in diisopropyl ether at 60 degrees C. The resolved products, obtained in good chemical yield (36-47%), could be easily separated.
Forró
Eniko
E
Institute of Pharmaceutical Chemistry, University of Szeged, P.O. Box 121, H-6701 Szeged, Hungary.
Fülöp
Ferenc
F
D000596:Amino Acids / Q000138:chemical synthesis*; D002384:Catalysis; D003500:Cyclization; D005656:Fungal Proteins; D008049:Lipase / Q000378:metabolism*; D012997:Solvents / Q000737:chemistry; D013237:Stereoisomerism; D047090:beta-Lactams / Q000138:chemical synthesis / Q000737:chemistry*
D000596:Amino Acids; D005656:Fungal Proteins; D012997:Solvents; D047090:beta-Lactams; D008049:Lipase; C431349:lipase B, Candida antarctica