Enantioselective synthesis of 2-arylpiperidines from chiral lactams. A concise synthesis of (?)-anabasine

Chemical Communications Pub Date: 2002-02-12 DOI: 10.1039/B200020M

Abstract

Cyclodehydration of achiral or racemic aryl-δ-oxoacids with (R)-phenylglycinol stereoselectively affords chiral non-racemic bicyclic lactams, from which the enantiodivergent synthesis of (R)- and (S)-2-phenylpiperidine, the diastereodivergent synthesis of cis- and trans-3-ethyl-2-phenylpiperidine, and the enantioselective synthesis of the piperidine alkaloid (?)-anabasine is reported.

Graphical abstract: Enantioselective synthesis of 2-arylpiperidines from chiral lactams. A concise synthesis of (?)-anabasine
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