Stereoselective copper-catalyzed Chan-Lam-Evans N-arylation of glucosamines with arylboronic acids at room temperature

被引：46

作者：

Bruneau, Alexandre ^{[1
]}

Brion, Jean-Daniel ^{[1
]}

Alami, Mouad ^{[1
]}

Messaoudi, Samir ^{[1
]}

机构：

[1] Univ Paris Sud, CNRS, BioCIS UMR 8076, Lab Chim Therapeut,LabEx LERMIT,Fac Pharm, F-92296 Chatenay Malabry, France

来源：

CHEMICAL COMMUNICATIONS | 2013年 / 49卷 / 75期

关键词：

COUPLING REACTIONS; NITROGEN; ANALOGS; ACCESS; UNIT;

D O I：

10.1039/c3cc44780d

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

An efficient and practical N-arylation of glycosylamines with substituted aryl boronic acids has been established. Using Cu(OAc)(2) and pyridine at room temperature under air atmosphere, the protocol proved to be general, and a variety of aryl N-glycosides have been prepared in good to excellent yields with exclusive beta selectivity.

引用

收藏

页码：8359 / 8361

页数：3

相关论文

共 34 条

[11] Role of copper species in the oxidative dimerization of arylboronic acids:: Synthesis of symmetrical biaryls [J].

Demir, AS ;

Reis, Ö ;

Emrullahoglu, M .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (26) :10130-10134

[12]

Du W., 2004, SYNTHETIC COMMUN, V34, P2987

[13] Glycobiology: Toward understanding the function of sugars [J].

Dwek, RA .

CHEMICAL REVIEWS, 1996, 96 (02) :683-720

[14] Synthesis and antiproliferative activity of selenoindirubins and selenoindirubin-N-glycosides [J].

Erben, Friedrich ;

Kleeblatt, Dennis ;

Sonneck, Marcel ;

Hein, Martin ;

Feist, Holger ;

Fahrenwaldt, Thomas ;

Fischer, Christine ;

Matin, Abdul ;

Iqbal, Jamshed ;

Ploetz, Michael ;

Eberle, Juergen ;

Langer, Peter .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2013, 11 (24) :3963-3978

[15] Synthesis of diaryl ethers through the copper-promoted arylation of phenols with arylboronic acids. An expedient synthesis of thyroxine [J].

Evans, DA ;

Katz, JL ;

West, TR .

TETRAHEDRON LETTERS, 1998, 39 (19) :2937-2940

[16] Chemical Synthesis of N-Aryl Glycosides [J].

Fosso, Marina Y. ;

Nziko, V. P. N. ;

Chang, Cheng-Wei Tom .

JOURNAL OF CARBOHYDRATE CHEMISTRY, 2012, 31 (08) :603-619

[17] How do multivalent glycodendrimers benefit from sulfur chemistry? [J].

Gingras, Marc ;

Chabre, Yoann M. ;

Roy, Myriam ;

Roy, Rene .

CHEMICAL SOCIETY REVIEWS, 2013, 42 (11) :4823-4841

[18] Synthesis of granulatimide bis-imide analogues [J].

Hénon, H ;

Messaoudi, S ;

Hugon, B ;

Anizon, F ;

Pfeiffer, B ;

Prudhomme, M .

TETRAHEDRON, 2005, 61 (23) :5599-5614

[19] Design of non-nucleoside inhibitors of HIV-1 reverse transcriptase with improved drug resistance properties. 1. [J].

Hopkins, AL ;

Ren, JS ;

Milton, J ;

Hazen, RJ ;

Chan, JH ;

Stuart, DI ;

Stammers, DK .

JOURNAL OF MEDICINAL CHEMISTRY, 2004, 47 (24) :5912-5922

[20] AIDS-DRIVEN NUCLEOSIDE CHEMISTRY [J].

HURYN, DM ;

OKABE, M .

CHEMICAL REVIEWS, 1992, 92 (08) :1745-1768

← 1 2 3 4 →