Enzymatic dynamic kinetic resolution of (+/-)-cis-N-(alkoxycarbonyl)cyclopentane-1,2-diamines based on spontaneous racemization.
Lipase B from Candida antarctica is an excellent catalyst for the enantioselective acetylation of different (+/-)-cis-N-(alkoxycarbonyl)cyclopentane-1,2-diamines. Depending on the alkoxycarbonyl group, a simple kinetic resolution (Boc-derivative) or an interesting dynamic kinetic resolution (DKR with Cbz-, Alloc, and ethoxycarbonyl derivatives) has been developed. Racemization for the DKR occurred due to the N,N' intramolecular migration of the alkoxycarbonyl group.
Quijada
F Javier
FJ
Departamento de Química Orgánica e Inorgánica, and Instituto Universitario de Biotecnología de Asturias, Universidad de Oviedo, 33071 Oviedo, Spain.
Gotor
Vicente
V
Rebolledo
Francisca
F
D002384:Catalysis; D003517:Cyclopentanes / Q000138:chemical synthesis* / Q000737:chemistry; D003959:Diamines / Q000138:chemical synthesis* / Q000737:chemistry; D005656:Fungal Proteins; D007700:Kinetics; D008049:Lipase / Q000378:metabolism*; D015394:Molecular Structure; D013237:Stereoisomerism
D003517:Cyclopentanes; D003959:Diamines; D005656:Fungal Proteins; C467768:cyclopentane-1,2-diamine; D008049:Lipase; C431349:lipase B, Candida antarctica