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Issue 40, 2015
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IBX-mediated oxidation of unactivated cyclic amines: application in highly diastereoselective oxidative Ugi-type and aza-Friedel–Crafts reactions

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Abstract

The first o-iodoxybenzoic acid (IBX) mediated oxidation of unactivated amines to imines is described. A range of meso-pyrrolidines were shown to be suitable substrates. The chemical space was further explored with one-pot oxidative Ugi-type and aza-Friedel–Crafts reactions, which proved to be highly diastereoselective.

Graphical abstract: IBX-mediated oxidation of unactivated cyclic amines: application in highly diastereoselective oxidative Ugi-type and aza-Friedel–Crafts reactions

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Publication details

The article was received on 23 Jul 2015, accepted on 07 Sep 2015 and first published on 08 Sep 2015


Article type: Communication
DOI: 10.1039/C5OB01519G
Citation: Org. Biomol. Chem., 2015,13, 10108-10112
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    IBX-mediated oxidation of unactivated cyclic amines: application in highly diastereoselective oxidative Ugi-type and aza-Friedel–Crafts reactions

    C. de Graaff, L. Bensch, M. J. van Lint, E. Ruijter and R. V. A. Orru, Org. Biomol. Chem., 2015, 13, 10108
    DOI: 10.1039/C5OB01519G

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