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

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

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 ald...

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Published in:Journal of the American Chemical Society Vol. 136; no. 3; pp. 890 - 893
Main Authors: Wickens, Zachary K, Skakuj, Kacper, Morandi, Bill, Grubbs, Robert H
Format: Journal Article
Language:English
Published: United States American Chemical Society 22-01-2014
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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.
AbstractList 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.
Author Grubbs, Robert H
Morandi, Bill
Skakuj, Kacper
Wickens, Zachary K
AuthorAffiliation California Institute of Technology
Arnold and Mabel Beckman Laboratory of Chemical Synthesis, Division of Chemistry and Chemical Engineering
AuthorAffiliation_xml – name: Arnold and Mabel Beckman Laboratory of Chemical Synthesis, Division of Chemistry and Chemical Engineering
– name: California Institute of Technology
Author_xml – sequence: 1
  givenname: Zachary K
  surname: Wickens
  fullname: Wickens, Zachary K
– sequence: 2
  givenname: Kacper
  surname: Skakuj
  fullname: Skakuj, Kacper
– sequence: 3
  givenname: Bill
  surname: Morandi
  fullname: Morandi, Bill
– sequence: 4
  givenname: Robert H
  surname: Grubbs
  fullname: Grubbs, Robert H
  email: rhg@caltech.edu
BackLink https://www.ncbi.nlm.nih.gov/pubmed/24410719$$D View this record in MEDLINE/PubMed
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Snippet The aldehyde-selective oxidation of alkenes bearing diverse oxygen groups in the allylic and homoallylic position was accomplished with a nitrite-modified...
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Title Catalyst-Controlled Wacker-Type Oxidation: Facile Access to Functionalized Aldehydes
URI http://dx.doi.org/10.1021/ja411749k
https://www.ncbi.nlm.nih.gov/pubmed/24410719
https://search.proquest.com/docview/1492674418
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