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Aziridination of Cyclic Nitrones Targeting Constrained Iminosugars.

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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… Click to show full abstract

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.

Keywords: constrained iminosugars; nitrones targeting; cyclic nitrones; targeting constrained; aziridination cyclic

Journal Title: Organic letters
Year Published: 2017

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