An unusual stereoselectivity in the anomeric substitution with carbamates promoted by HNTf2.
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.
Ko
Changhong
C
Division of Pharmaceutical Sciences and Department of Chemistry, Rennebohm Hall, 777 Highland Avenue University of Wisconsin, Madison, WI 53705-2222, USA.
Hsung
Richard P
RP
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
D000588:Amines; D002219:Carbamates; D003512:Cyclohexanones; D011522:Protons; C518058:triflimide