A versatile, three-component-reaction route to N-glycosylamines

[GRAPHICS] Under the agency of N-bromosuccinimide, n-pentenyl glycosides, acetonitrile, and carboxylic acids participate in th ree-component-reactions that afford N-acylated glycosylamines. The procedure tolerates diverse donors, and C2-tetrachlorophthalimido and CP-azido groups effectively control anomeric stereoselectivity, Success of the procedure does not appear to depend on the acid's strength, but for an aromatic acid, substitution pattern affects the rate, while the presence of a lone pair on the para substituent inhibits the process.