Amidoglycosylation via metal-catalyzed internal nitrogen atom delivery.
[reaction: see text] Rhodium and copper acyl nitrenoids are likely intermediates in amidoglycosylation reactions of allal 3-carbamates. Iodine(III)-mediated nitrenoid formation, interaction of this species with the glycal enol ether pi-system, and highly beta-stereoselective glycosylation occur in a one-pot process that requires no additional Lewis acid activation.
Levites-Agababa
Elana
E
Department of Chemistry, Barnard College, 3009 Broadway, New York, New York 10027, USA.
Menhaji
Elnaz
E
Perlson
Lisa N
LN
Rojas
Christian M
CM
D000606:Amino Sugars / Q000138:chemical synthesis* / Q000737:chemistry; D002219:Carbamates / Q000737:chemistry; D002384:Catalysis; D003300:Copper / Q000737:chemistry; D006031:Glycosylation; D012238:Rhodium / Q000737:chemistry
D000606:Amino Sugars; D002219:Carbamates; D003300:Copper; D012238:Rhodium