Issue 5, 2012
From the journal:

Organic & Biomolecular Chemistry

Stereoselective synthesis of N-aryl proline amides by biotransformation–Ugi-Smiles sequence†‡

Anass Znabet,a   Sara Blanken,a   Elwin Janssen,a   Frans J. J. de Kanter,a   Madeleine Helliwell,b   Nicholas J. Turner,c   Eelco Ruijter*a  and  Romano V. A. Orru*a  

* Corresponding authors

a Department of Chemistry & Pharmaceutical Sciences and Amsterdam Institute of Molecules, Medicines and Systems, VU University Amsterdam, De Boelelaan 1083, the Netherlands
E-mail: r.v.a.orru@vu.nl;e.ruijter@vu.nl
Fax: +31 20 5987488
Tel: +31 20 5987447

b School of Chemistry, University of Manchester, Brunswick Street, Manchester, UK

c School of Chemistry, University of Manchester, Manchester Interdisciplinary Biocentre, 131 Princess Street, Manchester, UK

Abstract

An efficient combination of MAO-N-catalyzed desymmetrization of cyclic meso-amines with Ugi-Smiles multicomponent chemistry produced optically pure N-aryl proline amides. This method represents the first report of a fully asymmetric Ugi-Smiles process.

Graphical abstract: Stereoselective synthesis of N-aryl proline amides by biotransformation–Ugi-Smiles sequence

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Article information

DOI
https://doi.org/10.1039/C1OB06699D
Article type
Communication
Submitted
07 Oct 2011
Accepted
10 Nov 2011
First published
16 Nov 2011

Org. Biomol. Chem., 2012,10, 941-944

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Stereoselective synthesis of N-aryl proline amides by biotransformation–Ugi-Smiles sequence

A. Znabet, S. Blanken, E. Janssen, F. J. J. de Kanter, M. Helliwell, N. J. Turner, E. Ruijter and R. V. A. Orru, Org. Biomol. Chem., 2012, 10, 941 DOI: 10.1039/C1OB06699D

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