title: Spontaneous enzymatically mediated dynamic kinetic resolution of 8-amino-5,6,7,8-tetrahydroquinoline.
abstract: A spontaneous dynamic kinetic resolution of 8-amino-5,6,7,8-tetrahydroquinoline 1 was observed in the presence of Candida antarctica Lipase B, in which a >60% yield of (R)-acetamide [(R)-2] was isolated from the racemic amine. The spontaneous formation of ketone 3, followed by a condensation/hydrolysis sequence with the remaining (S)-amine 1, via enamine 4, provides the necessary racemization pathway.
authors.affiliation: AnorMED Inc., #200-20353 64th Avenue, Langley, BC, Canada V2Y 1N5. jcrawford@anormed.com
authors.forename: Jason B
authors.initials: JB
authors.lastname: Crawford
authors.forename: Renato T
authors.initials: RT
authors.lastname: Skerlj
authors.forename: Gary J
authors.initials: GJ
authors.lastname: Bridger
mesh_terms: D000081:Acetamides / Q000138:chemical synthesis / Q000737:chemistry; D002175:Candida / Q000201:enzymology; D007700:Kinetics; D008049:Lipase / Q000737:chemistry*; D015394:Molecular Structure; D011804:Quinolines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D013997:Time Factors
chemical_list: C518116:8-amino-5,6,7,8-tetrahydroquinoline; D000081:Acetamides; D011804:Quinolines; C030686:acetamide; D008049:Lipase