- Stereocontrolled intramolecular aziridination of glycate: Ready access to aminoglycosides and mechanistic insights from DFT studies
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Stereocontrolled intramolecular aziridination of the glycal-derived sulfamates offers a highly efficient strategy to divergently prepare aminoglycosides. Rhodium-catalyzed nitrogen-atom transfer to C=C bonds formed semistable aziridines, which were subjected to various nucleophiles (C, O, S, and N) to give cyclic sulfamate-containing aminosugar derivatives selectively. The second nucleophilic displacement of sulfonyloxy moieties of [1,2,3]-oxathiazepane-2,2-dioxides allows straightforward access to aminoglycosides with selective α- or β-linkages. This approach is operationally simple, complements existing methods, and is a versatile protocol for the synthesis of polyfunctionalized amino sugars. In addition, the mechanism of the rhodium-catalyzed intramolecular aziridination of glycals and its ring-opening reaction was extensively studied by using DFT calculations.
- Lorpitthaya, Rujee,Xie, Zhi-Zhong,Kuo, Jer-Lai,Liu, Xue-Wei
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scheme or table
p. 1561 - 1570
(2009/04/06)
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- A New General Route to the Synthesis of Bicyclic Synthons from Glycals
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Iodonium sym-dicollidine perchlorate (IDCP: bis(2,4,6-trimethylpyridine)iodine(1+) perchlorate) mediated intramolecular iodoalkoxylation of 3,4-di-O-substituted glycals 9a-14f gives rise to synthetically useful chiral bicyclic synthons 15a-20f respectivel
- Mereyala, Hari Babu,Venkataramanaiah, Kanamarlapudi C
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p. 1953 - 1966
(2007/10/02)
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