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Amidoglycosylation via metal-catalyzed internal nitrogen atom delivery
Elana Levites-Agababa1, Elnaz Menhaji, Lisa N Perlson
1Department of Chemistry, Barnard College, 3009 Broadway, New York, New York 10027, USA.
Organic Letters
|March 1, 2002
Abstract:
[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.