Highly stereoselective synthesis of aminoglycosides via rhodium-catalyzed and substrate-controlled aziridination of glycals

Rujee Lorpitthaya; K. B. Sophy; Jer-Lai Kuo; Xue-Wei Liu

doi:10.1039/B823099B

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Organic & Biomolecular Chemistry

Issue 7, 2009

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Highly stereoselective synthesis of aminoglycosides via rhodium-catalyzed and substrate-controlled aziridination of glycals

Rujee Lorpitthaya , K. B. Sophy , Jer-Lai Kuo and Xue-Wei Liu

Org. Biomol. Chem., 2009, 7, 1284-1287

DOI: 10.1039/B823099B
Received 22 Dec 2008, Accepted 29 Jan 2009
First published on the web 11 Feb 2009

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Abstract
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The flexible installations of a sulfamate ester on a glycal scaffold at C3, C4, or C6 approaching α- or β-aminoglycosides is communicated. A variety of glycal acceptors (O, S, and N) were applied, enhancing the utility of this method as an operationally simple protocol for the stereoselective synthesis of polyfunctionalized α- or β- aminosaccharides.

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Organic & Biomolecular Chemistry

Highly stereoselective synthesis of aminoglycosides via rhodium-catalyzed and substrate-controlled aziridination of glycals

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