Stereoselective rearrangement of trichloroacetimidates: application to the synthesis of alpha-glycosyl ureas.
A new method for the stereoselective synthesis of alpha-glycosyl ureas, via nickel-catalyzed [1,3]-rearrangement of glycosyl trichloroacetimidates, has been developed. The alpha-stereoselectivity at the anomeric carbon of the resulting trichloroacetamides depends on the nature of the cationic nickel catalyst. This method is applicable to a number of trichloroacetimidate substrates. The alpha-glycosyl trichloroacetamides can be directly converted into alpha-glycosyl ureas in the presence of amines. In all cases, the stereochemical integrity at the urea linkages remains intact.
Park
Nathaniel H
NH
Department of Chemistry and Biochemistry, Montana State University, Bozeman, Montana 59717, USA.
Nguyen
Hien M
HM
D000081:Acetamides; D002384:Catalysis; D062845:Chloroacetates; D020650:Combinatorial Chemistry Techniques; D006027:Glycosides / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D009532:Nickel / Q000737:chemistry; D013237:Stereoisomerism; D014238:Trichloroacetic Acid / Q000737:chemistry; D014508:Urea / Q000138:chemical synthesis* / Q000737:chemistry
D000081:Acetamides; D062845:Chloroacetates; D006027:Glycosides; D014238:Trichloroacetic Acid; D009532:Nickel; D014508:Urea; C009528:trichloroacetamide