An expedient procedure for the oxidative cleavage of olefinic bonds with PhI(OAc)2, NMO, and catalytic OsO4.
PhI(OAc)(2) in the presence of OsO(4) (cat.) and 2,6-lutidine cleaves olefinic bonds to yield the corresponding carbonyl compounds, albeit, in some cases, with alpha-hydroxy ketones as byproduct. A more practical and clean protocol to effect oxidative cleavage of olefinic bonds involves NMO, OsO(4) (cat.), 2,6-lutidine, and PhI(OAc)(2).
Nicolaou
K C
KC
Department of Chemistry and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, USA. kcn@scripps.edu
Adsool
Vikrant A
VA
Hale
Christopher R H
CR
D000085:Acetates / Q000737:chemistry*; D000447:Aldehydes / Q000138:chemical synthesis / Q000737:chemistry; D000475:Alkenes / Q000737:chemistry*; D002384:Catalysis; D003497:Cyclic N-Oxides / Q000737:chemistry*; D007462:Iodobenzenes / Q000737:chemistry*; D007659:Ketones / Q000138:chemical synthesis / Q000737:chemistry; D015394:Molecular Structure; D009025:Morpholines / Q000737:chemistry*; D009993:Osmium Tetroxide / Q000737:chemistry*; D010084:Oxidation-Reduction; D013237:Stereoisomerism
D000085:Acetates; D000447:Aldehydes; D000475:Alkenes; D003497:Cyclic N-Oxides; D007462:Iodobenzenes; D007659:Ketones; D009025:Morpholines; C008857:phenyliodosodiacetate; C067960:4-methylmorpholine N-oxide; D009993:Osmium Tetroxide