Spontaneous enzymatically mediated dynamic kinetic resolution of 8-amino-5,6,7,8-tetrahydroquinoline.
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.
Crawford
Jason B
JB
AnorMED Inc., #200-20353 64th Avenue, Langley, BC, Canada V2Y 1N5. jcrawford@anormed.com
Skerlj
Renato T
RT
Bridger
Gary J
GJ
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
C518116:8-amino-5,6,7,8-tetrahydroquinoline; D000081:Acetamides; D011804:Quinolines; C030686:acetamide; D008049:Lipase