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.

This study demonstrates a spontaneous enzymatic resolution of 8-amino-5,6,7,8-tetrahydroquinoline 1, yielding (R)-acetamide and providing a racemization pathway for the remaining (S)-amine 1.

Paper

Spontaneous enzymatically mediated dynamic kinetic resolution of 8-amino-5,6,7,8-tetrahydroquinoline.

References

Citations