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

K. C. Nicolaou*, Vikrant A. Adsool and Christopher R. H. Hale

*Department of Chemistry and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, Email: kcnscripps.edu

K. C. Nicolaou, V. A. Adsool, C. R. H. Hale, Org. Lett., 2010, 12, 1552-1555.

DOI: 10.1021/ol100290a

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Abstract

The use of PhI(OAc)₂ in dichloromethane enables a clean oxidative cleavage of 1,2-diols to aldehydes. In the presence of OsO₄ as catalyst, NMO and 2,6-lutidine, olefinic bonds can be cleaved in acetone/water to yield the corresponding carbonyl compounds.

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Key Words

Aldehydes (Oxidation of Alcohols, Cleavage of Alkenes), Ketones (Cleavage of Alkenes), Iodosobenzene Diacetate, N-Methylmorpholine-N-Oxide

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ID: J54-Y2010-0980