Stereoselective copper-catalyzed Chan-Lam-Evans N-arylation of glucosamines with arylboronic acids at room temperature.
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 β selectivity.
Univ Paris-Sud, CNRS, BioCIS-UMR 8076, Laboratoire de Chimie Thérapeutique, LabEx LERMIT, Faculté de Pharmacie, 5 rue J.-B. Clément, Châtenay-Malabry, F-92296, France. samir.messaoudi@u-psud.fr mouad.alami@u-psud.fr.
Alexandre
A
Bruneau
Jean-Daniel
JD
Brion
Mouad
M
Alami
Samir
S
Messaoudi
D001897:Boronic Acids / Q000737:chemistry*; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D005944:Glucosamine / Q000737:chemistry*; D011725:Pyridines / Q000737:chemistry; D013696:Temperature
D001897:Boronic Acids; D011725:Pyridines; D003300:Copper; D005944:Glucosamine; C023666:pyridine