Add time:08/26/2019         Source:sciencedirect.com

The present study describes aza-Michael addition reactions of 4-aroylpent-4-enoic acids with (R)-phenylglycinol. Subsequent spontaneous lactamization yielded the corresponding piperidin-2-ones, which can selectively crystallize in very high diastereomeric purity. These are useful intermediates in the stereoselective syntheses of diverse 3-benzylpiperidines, as herein demonstrated by a chromatography-free and straightforward Gram-scale synthesis of (R)-3-benzylpiperidine hydrochloride.

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