Dynamic Kinetic Resolution of Racemic γ-Aryl-δ-oxoesters. Enantioselective Synthesis of 3-Arylpiperidines
The Journal of Organic Chemistry2002Vol. 67(15), pp. 5343–5351
Citations Over TimeTop 10% of 2002 papers
Mercedes Amat, Margalida Cantó, Núria Llor, Carmen Escolano, Elı́es Molins, Enrique Espinosa, Joan Bosch
Abstract
Cyclodehydration of racemic gamma-aryl-delta-oxoesters with (R)- or (S)-phenylglycinol stereoselectively affords bicyclic delta-lactams, in a process that involves a dynamic kinetic resolution. Subsequent reduction of these lactams leads to enantiopure 3-arylpiperidines. Starting from racemic aldehyde esters, this short sequence has been applied to the synthesis of (R)-3-phenylpiperidine and the antipsychotic drug (-)-3-PPP (an (S)-3-arylpiperidine), whereas starting from racemic ketone esters enantiopure cis-2-alkyl-3-arylpiperidines are prepared.
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