Issue 40, 2015
From the journal:

Organic & Biomolecular Chemistry

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

C. de Graaff,a   L. Bensch,a   Matthijs J. van Lint,a   E. Ruijtera  and  R. V. A. Orru*a  

* Corresponding authors

a Department of Chemistry & Pharmaceutical Sciences and Amsterdam Institute for Molecules Medicines and Systems (AIMMS), VU University Amsterdam, De Boelelaan 1083, 1081 HV Amsterdam, The Netherlands
E-mail: r.v.a.orru@vu.nl

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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Article information

DOI
https://doi.org/10.1039/C5OB01519G
Article type
Communication
Submitted
23 Jul 2015
Accepted
07 Sep 2015
First published
08 Sep 2015
This article is Open Access
Creative Commons BY license

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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