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Catalyst-Controlled Wacker-Type Oxidation: Facile Access to Functionalized Aldehydes

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. http://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
Related URLs:
URLURL TypeDescription
http://dx.doi.org/10.1021/ja411749kDOIArticle
http://pubs.acs.org/doi/abs/10.1021/ja411749kPublisherArticle
ORCID:
AuthorORCID
Grubbs, Robert H.0000-0002-0057-7817
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.
Funders:
Funding AgencyGrant Number
Gordon and Betty Moore FoundationUNSPECIFIED
NSFUNSPECIFIED
Swiss National Science Foundation (SNSF)UNSPECIFIED
Record Number:CaltechAUTHORS:20140122-102842387
Persistent URL:http://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:07 Dec 2016 23:12

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