Asymmetric synthesis .39. Synthesis of 3-substituted piperidin-2-ones from chiral non-racemic lactams.

被引：16

作者：

Micouin, L

Bonin, M

Cherrier, MP

Mazurier, A

Tomas, A

Quirion, JC

Husson, HP

机构：

[1] UNIV PARIS 05,FAC SCI PHARMACEUT & BIOL,CNRS,CHIM THERAPEUT LAB,F-75270 PARIS 06,FRANCE

[2] UNIV PARIS 05,FAC SCI PHARMACEUT & BIOL,PHYS LAB,F-75270 PARIS 06,FRANCE

来源：

TETRAHEDRON | 1996年 / 52卷 / 22期

关键词：

D O I：

10.1016/S0040-4020(96)00339-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A series of 3-substituted piperidines in enantiomerically pure form has been synthesized from lactam 1 via the bromo derivative 2i. t-Butyl acetate and 5-methylpyridine derivatives 2g and 2h were obtained optically pure by direct alkylation of 1 with corresponding halides. Azido, amino or benzyloxy products were obtained by diastereoselective substitution of 2i. Copyright (C) 1996 Elsevier Science Ltd

引用

页码：7719 / 7726

页数：8

共 13 条

[1] DAVIS FA, 1992, CHEM REV, V92, P913
[2] DISCOVERY OF A POTENT SUBSTANCE-P ANTAGONIST - RECOGNITION OF THE KEY MOLECULAR DETERMINANT
DESAI, MC
LEFKOWITZ, SL
THADEIO, PF
LONGO, KP
SNIDER, RM
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 1992, 35 (26) : 4911 - 4913
[3] STEREOSELECTIVE AMINATION OF CHIRAL ENOLATES - A NEW APPROACH TO THE ASYMMETRIC-SYNTHESIS OF ALPHA-HYDRAZINO AND ALPHA-AMINO-ACID DERIVATIVES
EVANS, DA
BRITTON, TC
DOROW, RL
DELLARIA, JF
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (20) : 6395 - 6397
[4] THE ASYMMETRIC-SYNTHESIS OF ALPHA-AMINO-ACIDS - ELECTROPHILIC AZIDATION OF CHIRAL IMIDE ENOLATES, A PRACTICAL APPROACH TO THE SYNTHESIS OF (R)-ALPHA-AZIDO AND (S)-ALPHA-AZIDO CARBOXYLIC-ACIDS
EVANS, DA
BRITTON, TC
ELLMAN, JA
DOROW, RL
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (10) : 4011 - 4030
[5] PIPERIDINE-ETHER BASED HNK(1) ANTAGONISTS .1. DETERMINATION OF THE RELATIVE AND ABSOLUTE STEREOCHEMICAL REQUIREMENTS
HARRISON, T
WILLIAMS, BJ
SWAIN, CJ
BALL, RG
[J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1994, 4 (21) : 2545 - 2550
[6] ASYMMETRIC-SYNTHESIS .30. SYNTHESIS OF 3-SUBSTITUTED PIPERIDINES FROM CHIRAL NON-RACEMIC LACTAMS
MICOUIN, L
VAREA, T
RICHE, C
CHIARONI, A
QUIRION, JC
HUSSON, HP
[J]. TETRAHEDRON LETTERS, 1994, 35 (16) : 2529 - 2532
[7] MICOUIN L, IN PRESS SYNTHETIC C
[8] ASYMMETRIC-SYNTHESIS .31. SYNTHESIS OF 2-SUBSTITUTED PIPERAZINES FROM CHIRAL NON-RACEMIC LACTAMS
SCHANEN, V
RICHE, C
CHIARONI, A
QUIRION, JC
HUSSON, HP
[J]. TETRAHEDRON LETTERS, 1994, 35 (16) : 2533 - 2536
[9] SCHANEN V, IN PRESS SYNTHESIS
[10] Sheldrick G.M., 1986, SHELX86 PROGRAM SOLU

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