Abstract
| - Cyclodehydration of racemic γ-aryl-δ-oxoesters with (R)- or (S)-phenylglycinol stereoselectivelyaffords bicyclic δ-lactams, in a process that involves a dynamic kinetic resolution. Subsequentreduction of these lactams leads to enantiopure 3-arylpiperidines. Starting from racemic aldehydeesters, this short sequence has been applied to the synthesis of (R)-3-phenylpiperidine and theantipsychotic drug (−)-3-PPP (an (S)-3-arylpiperidine), whereas starting from racemic ketone estersenantiopure cis-2-alkyl-3-arylpiperidines are prepared.
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