We are grateful for the generous financial support from the Singapore National Research Foundation (NRF), the Singapore Economic Development Board (EDB), GlaxoSmithKline (GSK), and the Nanyang Technological University (NTU); Dr. Y. Li and Dr. R. Ganguly (X-ray structure, NTU). We also appreciate the thoughtful suggestions from the referees.
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Communication
Facile Access to Chiral Ketones through Metal-Free Oxidative C![[BOND]](http://onlinelibrarystatic.wiley.com/undisplayable_characters/00f8ff.gif)
C Bond Cleavage of Aldehydes by O2†
Article first published online: 17 JAN 2012
DOI: 10.1002/anie.201107473
Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Additional Information
How to Cite
Tiwari, B., Zhang, J. and Chi, Y. R. (2012), Facile Access to Chiral Ketones through Metal-Free Oxidative CC Bond Cleavage of Aldehydes by O2. Angew. Chem. Int. Ed., 51: 1911–1914. doi: 10.1002/anie.201107473
- †
Publication History
- Issue published online: 14 FEB 2012
- Article first published online: 17 JAN 2012
- Manuscript Revised: 17 NOV 2011
- Manuscript Received: 24 OCT 2011
Funded by
- Singapore National Research Foundation (NRF)
- Singapore Economic Development Board (EDB)
- GlaxoSmithKline (GSK)
- Nanyang Technological University (NTU)
Keywords:
- CC cleavage;
- enamines;
- ketones;
- oxygen;
- synthetic methods
Giving the metal the boot: The title reaction provides facile access to functionalized chiral ketones from chiral α,α′-disubstituted aldehydes in the presence of molecular oxygen (see scheme). The CC bond-cleavage approach offers an alternative or better method relative to the typical bond-forming strategies used in synthesizing chiral ketones.