We are grateful to the EPSRC and GlaxoSmithKline for support, and to Dr. Simon Peace for helpful discussions.
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Communication
Enantioselective Synthesis of an Atropisomeric Diaryl Ether†
Article first published online: 17 MAR 2008
DOI: 10.1002/anie.200705660
Copyright © 2008 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Additional Information
How to Cite
Clayden, J., Worrall, C., Moran, W. and Helliwell, M. (2008), Enantioselective Synthesis of an Atropisomeric Diaryl Ether. Angewandte Chemie International Edition, 47: 3234–3237. doi: 10.1002/anie.200705660
- †
Publication History
- Issue published online: 8 APR 2008
- Article first published online: 17 MAR 2008
- Manuscript Revised: 4 JAN 2008
- Manuscript Received: 11 DEC 2007
Funded by
- EPSRC
- GlaxoSmithKline
Keywords:
- atropisomerism;
- conformation analysis;
- diaryl ethers;
- sulfur
Graphical Abstract
Twisted ethers: Introduction of a bulky alkylsulfinyl substituent ortho to the C–O axis of a diaryl ether imposes a powerful conformational preference (see scheme). The preference persists upon oxidation of the sulfoxide to a sulfone, leading to dynamic thermodynamic resolution of the atropisomeric ether. This is the first enantioselective synthesis of an atropisomeric diaryl ether not forming part of a macrocyclic ring.