1032661-45-2Relevant academic research and scientific papers
Stereocontrolled intramolecular aziridination of glycate: Ready access to aminoglycosides and mechanistic insights from DFT studies
Lorpitthaya, Rujee,Xie, Zhi-Zhong,Kuo, Jer-Lai,Liu, Xue-Wei
experimental part, p. 1561 - 1570 (2009/04/06)
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.
