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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.
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Crawford et al. (2006) studied this question.
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