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
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
[1]  
Adel A.H., 1999, CARBOHYD RES, V315, P106
[2]   Syntheses, biochemical and biological evaluation of staurosporine analogues from the microbial metabolite rebeccamycin [J].
Anizon, F ;
Moreau, P ;
Sancelme, M ;
Voldoire, A ;
Prudhomme, M ;
Ollier, M ;
Severe, D ;
Riou, JF ;
Bailly, C ;
Fabbro, D ;
Meyer, T ;
Aubertin, AM .
BIOORGANIC & MEDICINAL CHEMISTRY, 1998, 6 (09) :1597-1604
[3]   A convenient and expeditious synthesis of 3-(N-substituted) aminocoumarins via palladium-catalyzed Buchwald-Hartwig coupling reaction [J].
Audisio, Davide ;
Messaoudi, Samir ;
Peyrat, Jean-Francois ;
Brion, Jean-Daniel ;
Alami, Mouad .
TETRAHEDRON LETTERS, 2007, 48 (39) :6928-6932
[4]   A General Copper Powder-Catalyzed Ullmann-Type Reaction of 3-Halo-4(1H)-quinolones With Various Nitrogen-Containing Nucleophiles [J].
Audisio, Davide ;
Messaoudi, Samir ;
Peyrat, Jean-Francois ;
Brion, Jean-Daniel ;
Alami, Mouad .
JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (12) :4995-5005
[5]   Palladium-Catalyzed Cross-Coupling Reaction of Thioglycosides with (Hetero)aryl Halides [J].
Brachet, Etienne ;
Brion, Jean-Daniel ;
Messaoudi, Samir ;
Alami, Mouad .
ADVANCED SYNTHESIS & CATALYSIS, 2013, 355 (2-3) :477-490
[6]   One-pot stereoselective synthesis of β-N-aryl-glycosides by N-glycosylation of aromatic amines:: application to the synthesis of tumor-associated carbohydrate antigen building blocks [J].
Bridiau, Nicolas ;
Benmansour, Moulay ;
Legoy, Marie Dominique ;
Maugard, Thierry .
TETRAHEDRON, 2007, 63 (19) :4178-4183
[7]   Multivalent glycoconjugate syntheses and applications using aromatic scaffolds [J].
Chabre, Yoann M. ;
Roy, Rene .
CHEMICAL SOCIETY REVIEWS, 2013, 42 (11) :4657-4708
[8]   New N- and O-arylations with phenylboronic acids and cupric acetate [J].
Chan, DMT ;
Monaco, KL ;
Wang, RP ;
Winters, MP .
TETRAHEDRON LETTERS, 1998, 39 (19) :2933-2936
[9]   Total Synthesis of Nucleoside Antibiotics Possessing Novel N-Glycoside Structures [J].
Chida, Noritaka .
JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 2008, 66 (11) :1105-1115
[10]   Antiviral drug discovery and development: Where chemistry meets with biomedicine [J].
De Clercq, E .
ANTIVIRAL RESEARCH, 2005, 67 (02) :56-75