Dynamic kinetic resolution of racemic γ-aryl-δ-oxoesters.: Enantioselective synthesis of 3-arylpiperidines

被引：71

作者：

Amat, M ^{[1
]}

Cantó, M

Llor, N

Escolano, C

Molins, E

Espinosa, E

Bosch, J

机构：

[1] Univ Barcelona, Fac Pharm, Organ Chem Lab, E-08028 Barcelona, Spain

[2] CSIC, Inst Ciencia Mat, Barcelona 08193, Spain

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2002年 / 67卷 / 15期

关键词：

D O I：

10.1021/jo025894f

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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.

引用

页码：5343 / 5351

页数：9

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