Wickens, Zachary K. and Skakuj, Kacper and Morandi, Bill and Grubbs, Robert H. (2014) Catalyst-Controlled Wacker-Type Oxidation: Facile Access to Functionalized Aldehydes. Journal of the American Chemical Society, 136 (3). pp. 890-893. ISSN 0002-7863. doi:10.1021/ja411749k. https://resolver.caltech.edu/CaltechAUTHORS:20140122-102842387
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Abstract
The aldehyde-selective oxidation of alkenes bearing diverse oxygen groups in the allylic and homoallylic position was accomplished with a nitrite-modified Wacker oxidation. Readily available oxygenated alkenes were oxidized in up to 88% aldehyde yield and as high as 97% aldehyde selectivity. The aldehyde-selective oxidation enabled the rapid, enantioselective synthesis of an important pharmaceutical agent, atomoxetine. Finally, the influence of proximal functional groups on this anti-Markovnikov reaction was explored, providing important preliminary mechanistic insight.
| Item Type: | Article | |||||||||
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| Additional Information: | © 2014 American Chemical Society. Published In Issue January 22, 2014; Article ASAP January 13, 2014; Just Accepted Manuscript January 06, 2014; Received: November 18, 2013. We acknowledge financial support from the Gordon and Betty Moore Foundation, the NSF, and the Swiss National Science Foundation for a fellowship to B.M. | |||||||||
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| Issue or Number: | 3 | |||||||||
| DOI: | 10.1021/ja411749k | |||||||||
| Record Number: | CaltechAUTHORS:20140122-102842387 | |||||||||
| Persistent URL: | https://resolver.caltech.edu/CaltechAUTHORS:20140122-102842387 | |||||||||
| Official Citation: | Wickens, Z. K., Skakuj, K., Morandi, B., & Grubbs, R. H. (2014). Catalyst-Controlled Wacker-Type Oxidation: Facile Access to Functionalized Aldehydes. Journal of the American Chemical Society, 136(3), 890-893. doi: 10.1021/ja411749k | |||||||||
| Usage Policy: | No commercial reproduction, distribution, display or performance rights in this work are provided. | |||||||||
| ID Code: | 43469 | |||||||||
| Collection: | CaltechAUTHORS | |||||||||
| Deposited By: | Tony Diaz | |||||||||
| Deposited On: | 29 Jan 2014 17:10 | |||||||||
| Last Modified: | 10 Nov 2021 16:38 |
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