Palladium-catalyzed glycal imidate rearrangement: formation of alpha- and beta-N-glycosyl trichloroacetamides.
A novel palladium(II)-catalyzed stereoselective synthesis of alpha- and beta-N-glycosyl trichloroacetamides has been developed. The alpha- and beta-selectivity at the anomeric carbon depends on the nature of the palladium-ligand catalyst. While the cationic palladium(II) promotes the alpha-selectivity, the neutral palladium(II) favors the beta-selectivity.
Yang
Jaemoon
J
Department of Chemistry and Biochemistry, Montana State University, Bozeman, Montana 59717, USA.
Mercer
Gregory J
GJ
Nguyen
Hien M
HM
D000081:Acetamides / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D006027:Glycosides / Q000737:chemistry; D007096:Imidoesters / Q000737:chemistry*; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry*; D013237:Stereoisomerism; D013329:Structure-Activity Relationship; D014508:Urea / Q000031:analogs & derivatives / Q000138:chemical synthesis
D000081:Acetamides; D006027:Glycosides; D007096:Imidoesters; C013874:chloroacetamide; D010165:Palladium; D014508:Urea