Published January 6, 2014
| Supplemental Material
Journal Article
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Catalyst-Controlled Wacker-Type Oxidation: Facile Access to Functionalized Aldehydes
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.
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.Attached Files
Supplemental Material - ja411749k_si_001.pdf
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ja411749k_si_001.pdf
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Additional details
- Eprint ID
- 43469
- DOI
- 10.1021/ja411749k
- Resolver ID
- CaltechAUTHORS:20140122-102842387
- Gordon and Betty Moore Foundation
- NSF
- Swiss National Science Foundation (SNSF)
- Created
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2014-01-29Created from EPrint's datestamp field
- Updated
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2021-11-10Created from EPrint's last_modified field