title: An unusual stereoselectivity in the anomeric substitution with carbamates promoted by HNTf2.
abstract: An unexpected stereoselective anomeric substitution with carbamates promoted by HNTf2 is described here. Our experiments suggest that the observed diastereoselectivity is a result of thermodynamic equilibration of protonated N-acyl aminals.
authors.affiliation: Division of Pharmaceutical Sciences and Department of Chemistry, Rennebohm Hall, 777 Highland Avenue University of Wisconsin, Madison, WI 53705-2222, USA.
authors.forename: Changhong
authors.initials: C
authors.lastname: Ko
authors.forename: Richard P
authors.initials: RP
authors.lastname: Hsung
mesh_terms: D000215:Acylation; D000588:Amines / Q000737:chemistry; D002219:Carbamates / Q000737:chemistry*; D018360:Crystallography, X-Ray; D003512:Cyclohexanones / Q000737:chemistry*; D006031:Glycosylation; D009682:Magnetic Resonance Spectroscopy; D008956:Models, Chemical; D011522:Protons; D013237:Stereoisomerism
chemical_list: D000588:Amines; D002219:Carbamates; D003512:Cyclohexanones; D011522:Protons; C518058:triflimide