Synthesis of Aromatic α-Aminoesters: Palladium-Catalyzed Long-Range Arylation of Primary Csp3-H Bonds

被引：131

作者：

Aspin, Sam ^{[1
]}

Goutierre, Anne-Sophie ^{[1
]}

Larini, Paolo ^{[1
]}

Jazzar, Rodolphe ^{[1
]}

Baudoin, Olivier ^{[1
]}

机构：

[1] Univ Lyon 1, CNRS UMR 5246, Inst Chim & Biochim Mol & Supramol, CPE Lyon, F-69622 Villeurbanne, France

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2012年 / 51卷 / 43期

关键词：

arylation; C?C coupling; C?H functionalization; palladium; synthetic methods; UNACTIVATED C(SP(3))-H BONDS; AMINO-ACID DERIVATIVES; C-H ARYLATION; GAMMA-ARYLATION; COUPLING REACTIONS; ROOM-TEMPERATURE; BETA-ARYLATION; ARYL CHLORIDES; ESTERS; LIGANDS;

D O I：

10.1002/anie.201206237

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Remote control: The title reaction for β-Iζ arylation of α-amino esters with aryl bromides is described. This reaction, which occurs selectively at the terminal position of linear alkyl chains, gives rise to synthetically useful (hetero)arylalanines and homologues after debenzylation (see scheme). Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

引用

收藏

页码：10808 / 10811

页数：4

相关论文

共 45 条

[31] New ligands for a general palladium-catalyzed amination of aryl and heteroaryl chlorides [J].

Rataboul, F ;

Zapf, A ;

Jackstell, R ;

Harkal, S ;

Riermeier, T ;

Monsees, A ;

Dingerdissen, U ;

Beller, M .

CHEMISTRY-A EUROPEAN JOURNAL, 2004, 10 (12) :2983-2990

[32] Novel acetoxylation and C-C coupling reactions at unactivated positions in α-amino acid derivatives [J].

Reddy, B. V. Subba ;

Reddy, Leleti Rajender ;

Corey, E. J. .

ORGANIC LETTERS, 2006, 8 (15) :3391-3394

[33]

Renaudat A., 2010, Angew. Chem. Int. Ed, V122, P7419

[34] Palladium-Catalyzed β Arylation of Carboxylic Esters [J].

Renaudat, Alice ;

Jean-Gerard, Ludivine ;

Jazzar, Rodolphe ;

Kefalidis, Christos E. ;

Clot, Eric ;

Baudoin, Olivier .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (40) :7261-7265

[35] Development and applications of amino acid derived organometallics [J].

Rilatt, I ;

Caggiano, L ;

Jackson, RFW .

SYNLETT, 2005, (18) :2701-2719

[36] Synthesis of unnatural amino acids via Suzuki cross-coupling of enantiopure vinyloxazolidine derivatives [J].

Sabat, M ;

Johnson, CR .

ORGANIC LETTERS, 2000, 2 (08) :1089-1092

[37]

Schulz T., 2009, ANGEW CHEM, V121, P936, DOI DOI 10.1002/ANGE.200804898

[38] Practical Imidazole-Based Phosphine Ligands for Selective Palladium-Catalyzed Hydroxylation of Aryl Halides [J].

Schulz, Thomas ;

Torborg, Christian ;

Schaeffner, Benjamin ;

Huang, Jun ;

Zapf, Alexander ;

Kadyrov, Renat ;

Boerner, Armin ;

Beller, Matthias .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (05) :918-921

[39] Highly Diastereoselective Arylations of Substituted Piperidines [J].

Seel, Stephanie ;

Thaler, Tobias ;

Takatsu, Keishi ;

Zhang, Cong ;

Zipse, Hendrik ;

Straub, Bernd F. ;

Mayer, Peter ;

Knochert, Paul .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (13) :4774-4777

[40] Palladium-Catalyzed Allylic Cross-Coupling Reactions of Primary and Secondary Homoallylic Electrophiles [J].

Stokes, Benjamin J. ;

Opra, Susanne M. ;

Sigman, Matthew S. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (28) :11408-11411

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