Glycosyl transfer to nitrogen via cycloaddition.
[formula: see text] This letter describes the reduction to practice of a novel concept for functionalization of the anomeric carbon of carbohydrates with a nitrogen substituent. Thus, bisheterodienes with a thiono sulfur terminus and a sulfonylimine terminus are shown to undergo cycloaddition smoothly and stereoselectively to three different glycals.
Li
B
B
Department of Chemistry, Hunter College/CUNY, New York 10021, USA.
Franck
R W
RW
Capozzi
G
G
Menichetti
S
S
Nativi
C
C
D005960:Glucosides / Q000138:chemical synthesis*; D006031:Glycosylation; D009584:Nitrogen / Q000737:chemistry*; D013237:Stereoisomerism; D013455:Sulfur / Q000737:chemistry
D005960:Glucosides; D013455:Sulfur; D009584:Nitrogen