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.

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De Graaff, C., Bensch, L., Van Lint, M. J., Ruijter, E., & Orru, R. V. A. (2015). IBX-mediated oxidation of unactivated cyclic amines: application in highly diastereoselective oxidative Ugi-type and aza-Friedel-Crafts reactions. Organic and Biomolecular Chemistry, 13(40), 10108–10112. https://doi.org/10.1039/c5ob01519g

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