Synthesis of Chiral Amino Acid Anilides by Ligand-Free Copper-Catalyzed Selective N-Arylation of Amino Acid Amides

被引:29
作者
Dong, Junyu [1 ]
Wang, Yan [1 ]
Xiang, Qinjie [1 ]
Lv, Xirui [1 ]
Weng, Wen [2 ]
Zeng, Qingle [1 ]
机构
[1] Chengdu Univ Technol, Inst Green Catalysis & Synth, Coll Mat & Chem & Chem Engn, Chengdu 610059, Peoples R China
[2] Zhangzhou Normal Univ, Dept Chem & Environm Sci, Zhangzhou 363000, Peoples R China
关键词
amino acid amides; amino acid anilides; chiral pool; copper; cross-coupling; TRANSFER HYDROGENATION REACTION; C-N; COUPLING REACTIONS; METAL-COMPLEXES; ARYL; AMINATION; FUNCTIONALIZATION; AMIDATION; PROLINE; ANALOGS;
D O I
10.1002/adsc.201200752
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
An atom-economic, practical and cost-effective protocol for synthesis of chiral amino acid anilides via ligand-free copper-catalyzed selective CN cross coupling of chiral amino acid amides and aryl halides, hetereoaryl halides and a vinyl bromide has been developed. No racemization occurred during the CN coupling. A plausible mechanism is proposed.
引用
收藏
页码:692 / 696
页数:5
相关论文
共 51 条
[1]   Chemoselective Peptidomimetic Ligation Using Thioacid Peptides and Aziridine Templates [J].
Assem, Naila ;
Natarajan, Aditya ;
Yudin, Andrei K. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (32) :10986-10987
[2]   Copper in cross-coupling reactions - The post-Ullmann chemistry [J].
Beletskaya, IP ;
Cheprakov, AV .
COORDINATION CHEMISTRY REVIEWS, 2004, 248 (21-24) :2337-2364
[3]   Facile access to isotopically labelled valylleucyl anilides as biomarkers for the quantification of hemoglobin adducts to toxic electrophiles [J].
Belov, VN ;
Müller, M ;
Ignatenko, O ;
Hallier, E ;
de Meijere, A .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2005, 2005 (23) :5094-5099
[4]   Amino acid derived enamides: Synthesis and aminopeptidase activity [J].
Cesati, Richard R., III ;
Dwyer, Greg ;
Jones, Reinaldo C. ;
Hayes, Megan P. ;
Yalamanchili, Padmaja ;
Casebier, David S. .
ORGANIC LETTERS, 2007, 9 (26) :5617-5620
[5]   Proline-based dipeptides with two amide units as organocatalyst for the asymmetric aldol reaction of cyclohexanone with aldehydes [J].
Chen, Fubin ;
Huang, Shi ;
Zhang, Hui ;
Liu, Fengying ;
Peng, Yungui .
TETRAHEDRON, 2008, 64 (40) :9585-9591
[6]  
Colburn R. W., 2010, U.S. Patent, Patent No. 2010048589
[7]   Synthesis of phenothiazines via ligand-free CuI-catalyzed cascade C-S and C-N coupling of aryl ortho-dihalides and ortho-aminobenzenethiols [J].
Dai, Chuan ;
Sun, Xiaofei ;
Tu, Xingzhao ;
Wu, Li ;
Zhan, Dan ;
Zeng, Qingle .
CHEMICAL COMMUNICATIONS, 2012, 48 (43) :5367-5369
[8]   COMPLEX-FORMATION EQUILIBRIA OF L-AMINO-ACID AMIDES WITH COPPER(II) IN AQUEOUS-SOLUTION [J].
DALLAVALLE, F ;
FISICARO, E ;
CORRADINI, R ;
MARCHELLI, R .
HELVETICA CHIMICA ACTA, 1989, 72 (07) :1479-1486
[9]   Ugi-Post Functionalization, from a Single Set of Ugi-Adducts to Two Distinct Heterocycles by Microwave-Assisted Palladium-Catalyzed Cyclizations: Tuning the Reaction Pathways by Ligand Switch [J].
Erb, William ;
Neuville, Luc ;
Zhu, Jieping .
JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (08) :3109-3115
[10]   Enantioselective nickel-catalyzed conjugate addition of dialkylzinc to chalcones using chiral α-amino amides [J].
Escorihuela, Jorge ;
Burguete, M. Isabel ;
Luis, Santiago V. .
TETRAHEDRON LETTERS, 2008, 49 (48) :6885-6888