Cross-Dehydrogenative Coupling Reactions by Transition-Metal and Aminocatalysis for the Synthesis of Amino Acid Derivatives

被引：236

作者：

Xie, Jin ^{[1
]}

Huang, Zhi-Zhen ^{[1
,2
]}

机构：

[1] Nanjing Univ, Coll Chem & Chem Engn, Key Lab Mesoscop Chem, MOE, Nanjing 210093, Peoples R China

[2] Nankai Univ, State Key Lab Elementoorgan Chem, Tianjin 300071, Peoples R China

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2010年 / 49卷 / 52期

基金：

中国国家自然科学基金;

关键词：

amino acids; C-H activation; cooperative catalysis; cross-coupling; organocatalysis; C-H BONDS; CATALYZED OXIDATIVE CYANATION; MANNICH-TYPE REACTION; HYDROGEN-PEROXIDE; TERTIARY-AMINES; GLYCINE DERIVATIVES; ALLYLIC ALKYLATION; SODIUM-CYANIDE; BENZYL ETHERS; ARYL HALIDES;

D O I：

10.1002/anie.201004940

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The direct approach: The title coupling reactions of N-aryl glycine esters with unmodified ketones occurred smoothly in the presence of tert-butyl hydroperoxide (TBHP) or 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) under mild conditions (see scheme). The oxidant used for C-H activation determined the selectivity of the reactions for a particular type of ketone substrate. Copyright © 2010 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

引用

页码：10181 / 10185

页数：5

共 62 条

[1] Asymmetric autocatalytic Mannich reaction in the presence of water and its implication in prebiotic chemistry [J].

Amedjkouh, Mohamed ;

Brandberg, Maria .

CHEMICAL COMMUNICATIONS, 2008, (26) :3043-3045

[2]

[Anonymous], ANGEW CHEM

[3] Catalytic stereoselective benzylic C-H functionalizations by oxidative C-H activation and organocatalysis [J].

Benfatti, Fides ;

Capdevila, Montse Guiteras ;

Zoli, Luca ;

Benedetto, Elena ;

Cozzi, Pier Giorgio .

CHEMICAL COMMUNICATIONS, 2009, (39) :5919-5921

[4] Copper-catalyzed oxidative coupling of benzylic C-H bonds with 1,3-dicarbonyl compounds [J].

Borduas, Nadine ;

Powell, David A. .

JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (19) :7822-7825

[5] The oxidative Mannich reaction catalyzed by dirhodium caprolactamate [J].

Catino, AJ ;

Nichols, JM ;

Nettles, BJ ;

Doyle, MP .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (17) :5648-5649

[6] Visible-Light Photoredox Catalysis: Aza-Henry Reactions via C-H Functionalization [J].

Condie, Allison G. ;

Gonzalez-Gomez, Jose C. ;

Stephenson, Corey R. J. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (05) :1464-+

[7] Copper-Catalyzed Cross-Dehydrogenative Coupling (CDC) of Alkynes and Benzylic C-H Bonds [J].

Correia, Camille A. ;

Li, Chao-Jun .

ADVANCED SYNTHESIS & CATALYSIS, 2010, 352 (09) :1446-1450

[8]

Deng G., 2008, ANGEW CHEM, V120, P6374

[9] Peroxide-mediated efficient addition of cycloalkanes to imines [J].

Deng, Guojun ;

Li, Chao-Jun .

TETRAHEDRON LETTERS, 2008, 49 (39) :5601-5604

[10] Ruthenium-catalyzed oxidative cross-coupling of chelating arenes and cycloalkanes [J].

Deng, Guojun ;

Zhao, Liang ;

Li, Chao-Jun .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (33) :6278-6282

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