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

被引：39

作者：

Amat, M ^{[1
]}

Cantó, M ^{[1
]}

Llor, N ^{[1
]}

Bosch, J ^{[1
]}

机构：

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

来源：

CHEMICAL COMMUNICATIONS | 2002年 / 05期

关键词：

D O I：

10.1039/b200020m

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Cyclodehydration of achiral or racemic aryl-delta-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.

引用

页码：526 / 527

页数：2

共 22 条

[1]

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

[2]

2-Y

[3] Conjugate addition of organocuprates to chiral bicyclic δ-lactams.: Enantioselective synthesis of cis-3,4-disubstituted and 3,4,5-trisubstituted piperidines [J].

Amat, M ;

Pérez, M ;

Llor, N ;

Bosch, J ;

Lago, E ;

Molins, E .

ORGANIC LETTERS, 2001, 3 (04) :611-614

[4] 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

[5]

Andrés JM, 2000, EUR J ORG CHEM, V2000, P1719

[6]

ANGLE SR, 1995, STUDIES NATURAL PROD, V6, P453

[7] Asymmetric routes to substituted piperidines [J].

Bailey, PD ;

Millwood, PA ;

Smith, PD .

CHEMICAL COMMUNICATIONS, 1998, (06) :633-640

[8]

Barco A, 2001, EUR J ORG CHEM, V2001, P975

[9]

DEGRAAFF GB, 1964, RECL TRAV CHIM PAY B, V83, P910

[10]

Felpin FX, 2000, SYNLETT, P1646

← 1 2 3 →