The Copper-Catalyzed Decarboxylative Coupling of the sp3-Hybridized Carbon Atoms of α-Amino Acids

被引：277

作者：

Bi, Hai-Peng ^{[1
,2
]}

Zhao, Liang ^{[2
]}

Liang, Yong-Min ^{[1
]}

Li, Chao-Jun ^{[2
]}

机构：

[1] Lanzhou Univ, State Key Lab Appl Organ Chem, Lanzhou 730000, Peoples R China

[2] McGill Univ, Dept Chem, Montreal, PQ H3A 2K6, Canada

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2009年 / 48卷 / 04期

基金：

加拿大自然科学与工程研究理事会;

关键词：

amino acids; copper; cross-coupling; decarboxylation; peroxides; C-H ACTIVATION; OXIDATIVE DECARBOXYLATION; AZOMETHINE YLIDES; CARBOXYLIC-ACIDS; ALKALOIDS; REARRANGEMENT; PYRROLIDINE; WATER; TRANSAMINATION; HETEROCYCLES;

D O I：

10.1002/anie.200805122

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(Chemical Equation Presented) Joined at the Cs: A novel intermolecular decarboxylative Csp3-Csp3, Csp3-C sp2, and Csp3-Csp coupling catalyzed by CuBr and using a-amino acids as starting materials has been developed (see scheme). Various functionalized nitrogen-containing compounds were obtained by this method. © 2009 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：792 / 795

页数：4

共 62 条

[1]

Bartlett P.A., 1984, ASYMMETRIC SYNTHESIS, V3, P411

[2] Synthesis of biaryls via decarboxylative Pd-catalyzed cross-coupling reaction [J].

Becht, Jean-Michel ;

Catala, Cedric ;

Le Drian, Claude ;

Wagner, Alain .

ORGANIC LETTERS, 2007, 9 (09) :1781-1783

[3] Synthesis of 2,3-disubstituted pyrrolidines and piperidines via one-pot oxidative decarboxylation-β-iodination of amino acids [J].

Boto, A ;

Hernández, R ;

de León, Y ;

Suárez, E .

JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (23) :7796-7803

[4] Synthesis of homoallylic sulfones through a decarboxylative Claisen rearrangement reaction [J].

Bourgeois, D ;

Craig, D ;

King, NP ;

Mountford, DM .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (04) :618-621

[5]

BOURGEOIS D, 2005, ANGEW CHEM, V117, P624

[6] Synthesis of homoallylic amines via the palladium-catalyzed decarboxylative coupling of amino acid derivatives [J].

Burger, Erin C. ;

Tunge, Jon A. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (31) :10002-10003

[7] STEREOCONTROLLED CYCLOFUNCTIONALIZATIONS OF DOUBLE-BONDS THROUGH HETEROCYCLIC INTERMEDIATES [J].

CARDILLO, G ;

ORENA, M .

TETRAHEDRON, 1990, 46 (10) :3321-3408

[8]

Cheeseman G.W. H., 1984, Comprehensive Heterocyclic Chemistry, V4, P89

[9] Intramolecular dipolar cycloaddition reactions of azomethine ylides [J].

Coldham, I ;

Hufton, R .

CHEMICAL REVIEWS, 2005, 105 (07) :2765-2809

[10] THE PICTET-SPENGLER CONDENSATION - A NEW DIRECTION FOR AN OLD REACTION [J].

COX, ED ;

COOK, JM .

CHEMICAL REVIEWS, 1995, 95 (06) :1797-1842

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