Financial support was provided by the NIHGMS (R01 GM078201-01-01), the French Ministry of Foreign Affairs (EGIDE, Lavoisier fellowship for M.A.), Merck and Amgen. The would like to thank J. W. L. Hammett for help with the described racemization studies. SOMO=singly occupied molecular orbital.
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Communication
Enantioselective Linchpin Catalysis by SOMO Catalysis: An Approach to the Asymmetric α-Chlorination of Aldehydes and Terminal Epoxide Formation†
Article first published online: 12 JUN 2009
DOI: 10.1002/anie.200901855
Copyright © 2009 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Additional Information
How to Cite
Amatore, M., Beeson, Teresa D., Brown, Sean P. and MacMillan, David W. C. (2009), Enantioselective Linchpin Catalysis by SOMO Catalysis: An Approach to the Asymmetric α-Chlorination of Aldehydes and Terminal Epoxide Formation. Angew. Chem. Int. Ed., 48: 5121–5124. doi: 10.1002/anie.200901855
- †
Publication History
- Issue published online: 25 JUN 2009
- Article first published online: 12 JUN 2009
- Manuscript Received: 6 APR 2009
Funded by
- NIHGMS. Grant Number: R01 GM078201-01-01
- French Ministry of Foreign Affairs
- Merck
- Amgen
Keywords:
- epoxidation;
- enantioselectivity;
- asymmetric catalysis;
- organocatalysis
Abstract
Time for SOme MOre: For the first time SOMO (singly occupied molecular orbital) activation has been exploited to allow a new approach to the α-chlorination of aldehydes. This transformation can be readily implemented as part of a linchpin catalysis approach to the enantioselective production of terminal epoxides.