4.8 Article

An Expedient Procedure for the Oxidative Cleavage of Olefinic Bonds with PhI(OAc)2, NMO, and Catalytic OsO4

Journal

ORGANIC LETTERS
Volume 12, Issue 7, Pages 1552-1555

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ol100290a

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Funding

  1. National Institutes of Health [AI 055475]
  2. National Science Foundation [CHE-0603217]
  3. NSF Graduate Research Fellowship

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PhI(OAc)(2) In the presence of OsO4 (cat.) and 2,6-lutidine cleaves olefinic bonds to yield the corresponding carbonyl compounds, albeit, in some cases, with a-hydroxy ketones as byproduct. A more practical and clean protocol to effect oxidative cleavage of olefinic bonds involves NMO, OsO4 (cat.), 2,6-lutidine, and PhI(OAc)(2).

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