Palladium-catalyzed coupling reaction of amino acids (esters) with aryl bromides and chlorides

被引：34

作者：

Ma, Fangfang ^{[1
]}

Xie, Xiaomin ^{[1
]}

Ding, Lina ^{[2
]}

Gao, Jinsheng ^{[2
]}

Zhang, Zhaoguo ^{[1
,3
]}

机构：

[1] Shanghai Jiao Tong Univ, Sch Chem & Chem Engn, Shanghai 200240, Peoples R China

[2] Heilongjiang Univ, Sch Chem Chem Engn & Mat, Harbin 150080, Peoples R China

[3] Chinese Acad Sci, Shanghai Inst Organ Chem, Shanghai 200032, Peoples R China

来源：

TETRAHEDRON | 2011年 / 67卷 / 48期

基金：

中国国家自然科学基金;

关键词：

Palladium; Monophosphine ligand; Inactive aryl halide; Amino acid; ENANTIOSPECIFIC SYNTHESIS; ASYMMETRIC-SYNTHESIS; PHOSPHINE-LIGANDS; HALIDES; ALPHA; AMINATION; BOND; BULKY; ELIMINATION; ARYLAMINES;

D O I：

10.1016/j.tet.2011.09.109

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The bulky and electron-rich MOP type ligands and Pd(dba)(2) combinations showed high efficiency for the coupling reactions of amino acids and inactive aryl halides to give N-aryl amino acids. Under the catalytic conditions, not only alpha-amino acids, but also beta-, gamma-, and delta-amino acids have been coupled with aryl chlorides in moderate to high yields; in the case of optically pure beta-amino acids as substrates, the optical purities of the coupling products retained. (C) 2011 Elsevier Ltd. All rights reserved.

引用

页码：9405 / 9410

页数：6

共 63 条

[1]

Adam J., 2010, [No title captured], Patent No. [Patent US2010/22518 Al, 2010, 201022518]

[2] Kinetics and mechanism of thermal gas-phase elimination of α and β (N-arylamino)propanoic acid:: experimental and theoretical analysis [J].

Al-Awadi, SA ;

Abdallah, MR ;

Hasan, MA ;

Al-Awadi, NA .

TETRAHEDRON, 2004, 60 (13) :3045-3049

[3]

ANTIPANOVA VE, 1986, J APPL CHEM-USSR+, V59, P211

[4] 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

[5] Practical Syntheses of Oxindole Derivatives: Chemical Development towards 2-(5-Chloro-2-oxo-2,3-dihydroindol-1-yl)acetamide and (S)-2-(5-Chloro-2-oxo-2,3-dihydroindol-1-yl)propionamide [J].

Broeders, Fabienne ;

Defrere, Laurent ;

Deltent, Marie-France ;

Driessens, Frank ;

Gilson, Frederic ;

Grooters, Luc ;

Ikonomakos, Xavier ;

Limauge, Frederic ;

Sergeef, Emmanuel ;

Verstraeten, Natacha .

ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2009, 13 (03) :442-449

[6] Industrial-scale palladium-catalyzed coupling of aryl halides and amines - A personal account [J].

Buchwald, SL ;

Mauger, C ;

Mignani, G ;

Scholz, U .

ADVANCED SYNTHESIS & CATALYSIS, 2006, 348 (1-2) :23-39

[7] Monoligated palladium species as catalysts in cross-coupling reactions [J].

Christmann, U ;

Vilar, R .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (03) :366-374

[8]

Coppola G.M., 1987, ASYMMETRIC SYNTHESIS

[9] Asymmetric synthesis of the cholesteryl ester transfer protein inhibitor torcetrapib [J].

Damon, David B. ;

Dugger, Robert W. ;

Hubbs, Stephen E. ;

Scott, Jill M. ;

Scott, Robert W. .

ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2006, 10 (03) :472-480

[10] N-aryl 2,6-dimethoxybiphenylalanine analogues as VLA-4 antagonists [J].

Doherty, GA ;

Kamenecka, T ;

McCauley, E ;

Van Riper, G ;

Mumford, RA ;

Tong, S ;

Hagmann, WK .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2002, 12 (05) :729-731

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