K.-S.M. would like to thank the Alexander von Humboldt Foundation for generous funding and support, and the Bräse group for the fond memories.
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Communication
The Acetal Concept: Regioselective Access to ortho,ortho-Diphenols via Dibenzo-1,3-dioxepines†
Article first published online: 23 NOV 2012
DOI: 10.1002/anie.201207485
Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Additional Information
How to Cite
Masters, K.-S. and Bräse, S. (2013), The Acetal Concept: Regioselective Access to ortho,ortho-Diphenols via Dibenzo-1,3-dioxepines . Angew. Chem. Int. Ed., 52: 866–869. doi: 10.1002/anie.201207485
- †
Publication History
- Issue published online: 11 JAN 2013
- Article first published online: 23 NOV 2012
- Manuscript Received: 16 SEP 2012
Funded by
- Alexander von Humboldt Foundation
Keywords:
- acetal tethers;
- biphenols;
- dioxepines;
- diphenols;
- radical cyclization
Traditional methods are ill-suited for the synthesis of ortho,ortho-biphenols, a structural motif found in many polyphenolic natural products, as well as synthetically useful compounds such as the chiral ligands binol, vapol, and vanol. The new route consists of a radical-based reaction of an acetal-tethered biphenyl ether substrate and subsequent hydrolytic cleavage of the dibenzo-1,3-dioxepine intermediate.