We thank Dr. Benson Kariuki (Cardiff University) for the X-ray analysis of 8, Grégory Bonnamain (University of Nantes, France) and Pierre-Henri Belin, (ESCOM, France) for assistance in the synthesis of some starting materials, and the EPSRC National Mass Spectrometry Service Centre, Swansea, for mass spectrometric data. We thank The Charles Wallace Pakistan Trust (U.F.) and Cardiff University for financial support.
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Highly Stereoselective Metal-Free Oxyaminations Using Chiral Hypervalent Iodine Reagents†
Article first published online: 25 JAN 2012
DOI: 10.1002/anie.201107703
Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Additional Information
How to Cite
Farid, U. and Wirth, T. (2012), Highly Stereoselective Metal-Free Oxyaminations Using Chiral Hypervalent Iodine Reagents. Angew. Chem. Int. Ed., 51: 3462–3465. doi: 10.1002/anie.201107703
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Publication History
- Issue published online: 27 MAR 2012
- Article first published online: 25 JAN 2012
- Manuscript Received: 1 NOV 2011
Funded by
- The Charles Wallace Pakistan Trust
- Cardiff University
Keywords:
- amino alcohols;
- aminohydroxylation;
- cyclization;
- hypervalent iodine;
- stereoselective synthesis
The ring and I: Hypervalent iodine compounds avoid the issues of toxicity or complicated ligands of many transition-metal-based systems. A highly enantioselective oxyamination of alkenes with N-sulfonyl ureas employing chiral, lactic acid-based hypervalent iodine reagents gives a facile synthesis of enantiomerically pure 2-arylproline derivatives (see scheme) for the first time.