Pd/Cu-catalyzed couplings of β-amino esters with aryl bromides.: Synthesis of chiral 1,2,3,4-tetrahydro-4-oxo-2-alkyl-1-quinolines

被引:17
作者
Ma, DW [1 ]
Jiang, JQ [1 ]
机构
[1] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Bioorgan & Nat Prod Chem, Shanghai 200032, Peoples R China
基金
中国国家自然科学基金;
关键词
D O I
10.1016/S0957-4166(98)00078-0
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
A new protocol to prepare chiral 1,2,3,4-tetrahydro-4-oxo-2-alkyl-1-quinolines has been developed. The key steps are Pd/Cu-catalyzed couplings of chiral beta-amino esters and aryl bromides, and intramolecular acylation. (C) 1998 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:1137 / 1142
页数:6
相关论文
共 22 条
[1]   Palladium-catalyzed synthesis of aryl-substituted polyamine compounds from aryl halides. [J].
Beletskaya, IP ;
Bessmertnykh, AG ;
Guilard, R .
TETRAHEDRON LETTERS, 1997, 38 (13) :2287-2290
[2]   First palladium-catalyzed aminations of aryl chlorides [J].
Beller, M ;
Riermeier, TH ;
Reisinger, CP ;
Herrmann, WA .
TETRAHEDRON LETTERS, 1997, 38 (12) :2073-2074
[3]   PALLADIUM-CATALYZED AMINATION OF ARYL HALIDES - CATALYSTS ON NEW ROUTES TO KNOWN TARGETS [J].
BELLER, M .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1995, 34 (12) :1316-1317
[4]  
CARDILLO G, 1996, CHEM SOC REV, P117
[5]   2-CARBOXYTETRAHYDROQUINOLINES - CONFORMATIONAL AND STEREOCHEMICAL REQUIREMENTS FOR ANTAGONISM OF THE GLYCINE SITE ON THE NMDA RECEPTOR [J].
CARLING, RW ;
LEESON, PD ;
MOSELEY, AM ;
BAKER, R ;
FOSTER, AC ;
GRIMWOOD, S ;
KEMP, JA ;
MARSHALL, GR .
JOURNAL OF MEDICINAL CHEMISTRY, 1992, 35 (11) :1942-1953
[6]   ASYMMETRIC-SYNTHESIS OF R-BETA-AMINO BUTANOIC ACID AND S-BETA-TYROSINE - HOMOCHIRAL LITHIUM AMIDE EQUIVALENTS FOR MICHAEL ADDITIONS TO ALPHA,BETA-UNSATURATED ESTERS [J].
DAVIES, SG ;
ICHIHARA, O .
TETRAHEDRON-ASYMMETRY, 1991, 2 (03) :183-186
[7]   A second-generation catalyst for aryl halide amination: Mixed secondary amines from aryl halides and primary amines catalyzed by (DPPF)PdCl2 [J].
Driver, MS ;
Hartwig, JF .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (30) :7217-7218
[8]   Palladium-catalyzed amination of aryl halides: Mechanism and rational catalyst design [J].
Hartwig, JF .
SYNLETT, 1997, (04) :329-+
[9]   THE GLYCINE SITE OF THE NMDA RECEPTOR - 5 YEARS ON [J].
KEMP, JA ;
LEESON, PD .
TRENDS IN PHARMACOLOGICAL SCIENCES, 1993, 14 (01) :20-25
[10]   Palladium-catalyzed amination of aryl triflates and importance of triflate addition rate [J].
Louie, J ;
Driver, MS ;
Hamann, BC ;
Hartwig, JF .
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (05) :1268-1273