4 years ago

Aziridination of Cyclic Nitrones Targeting Constrained Iminosugars

Aziridination of Cyclic Nitrones Targeting Constrained Iminosugars
Clara Aupic, Jean-François Poisson, Salia Tangara, Sandrine Py, Alice Kanazawa
Rare C-7-substituted aziridinyl iminosugars can be synthesized through a short reaction sequence involving 1,3-cycloaddition of cyclic nitrones with alkynes and a Baldwin rearrangement of isoxazolines into bicyclic 2-acylaziridines. The method is efficient and completely diastereoselective, producing stable aziridinyl iminosugars in high yields.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b02283

DOI: 10.1021/acs.orglett.7b02283

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