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

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.

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Item Permalink: https://hdl.handle.net/11858/00-001M-0000-0025-BAB2-9 Version Permalink: https://hdl.handle.net/11858/00-001M-0000-0025-BAB7-0
Genre: Journal Article

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 Creators:
Wickens, Zachary K.1, Author
Skakuj, Kacper1, Author
Morandi, Bill1, 2, Author           
Grubbs, Robert H.1, Author
Affiliations:
1old and Mabel Beckman Laboratory of Chemical Synthesis, Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, California 91125, United States, ou_persistent22              
2Research Group Morandi, Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_2040309              

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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.

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Language(s): eng - English
 Dates: 2014-01-062014
 Publication Status: Issued
 Pages: -
 Publishing info: -
 Table of Contents: -
 Rev. Type: Peer
 Identifiers: DOI: 10.1021/ja411749k
 Degree: -

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Title: Journal of the American Chemical Society
  Other : J. Am. Chem. Soc.
  Abbreviation : JACS
Source Genre: Journal
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Publ. Info: Washington, DC : American Chemical Society
Pages: - Volume / Issue: 136 (3) Sequence Number: - Start / End Page: 890 - 893 Identifier: ISSN: 0002-7863
CoNE: https://pure.mpg.de/cone/journals/resource/954925376870