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

共 54 条

[1] SYNTHESIS OF 2-HYDROXY-2-PHENYLETHYLAMINO DERIVATIVES AS POTENTIAL ALPHA-ADRENERGIC BLOCKING-AGENTS [J].

ALVAREZ, M ;

GRANADOS, R ;

LAVILLA, R ;

SALAS, M .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 1985, 22 (03) :745-750

[2] Enantioselective syntheses of the indole alkaloid (+)-R-decarbomethoxytetrahydrosecodine and its enantiomer [J].

Amat, M ;

Pshenichnyi, G ;

Bosch, J ;

Molins, E ;

Miravitlles, C .

TETRAHEDRON-ASYMMETRY, 1996, 7 (11) :3091-3094

[3] Synthesis of enantiopure piperidines. Total synthesis of (2R,6S)-2-methyl-6-propylpiperidine [(-)-dihydropinidine] [J].

Amat, M ;

Llor, H ;

Hidalgo, J ;

Hernandez, A ;

Bosch, J .

TETRAHEDRON-ASYMMETRY, 1996, 7 (04) :977-980

[4]

Amat M, 2002, ANGEW CHEM INT EDIT, V41, P335, DOI 10.1002/1521-3773(20020118)41:2<335::AID-ANIE335>3.0.CO

[5]

2-Y

[6] CHIRAL PRECURSORS FOR THE SYNTHESIS OF ENANTIOMERICALLY PURE PIPERIDINES - TOTAL SYNTHESIS OF (R)-(-)-CONIINE [J].

AMAT, M ;

LLOR, N ;

BOSCH, J .

TETRAHEDRON LETTERS, 1994, 35 (14) :2223-2226

[7] Enantioselective synthesis of the trans-2,6-dialkylpiperidine alkaloids (2R,6R)-lupetidine and (2R,6R)-solenopsin A [J].

Amat, M ;

Hidalgo, J ;

Llor, N ;

Bosch, J .

TETRAHEDRON-ASYMMETRY, 1998, 9 (14) :2419-2422

[8] Synthesis of enantiopure trans-3,4-disubstituted piperidines.: An enantiodivergent synthesis of (+)- and (-)-paroxetine [J].

Amat, M ;

Bosch, J ;

Hidalgo, J ;

Cantó, M ;

Pérez, M ;

Llor, N ;

Molins, E ;

Miravitlles, C ;

Orozco, M ;

Luque, J .

JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (10) :3074-3084

[9]

Angle S. R., 1995, STUD NAT PROD CHEM, V16, P453

[10] AN EFFICIENT RESOLUTION OF 3-PPP AND ASSIGNMENT OF THE ABSOLUTE-CONFIGURATION [J].

ARNOLD, W ;

DALY, JJ ;

IMHOF, R ;

KYBURZ, E .

TETRAHEDRON LETTERS, 1983, 24 (04) :343-346

← 1 2 3 4 5 6 →