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Synthesis of ketones by oxidation of alkenes

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Recent Literature

The OsO₄-catalyzed direct oxidation of olefins via the carbon-carbon cleavage of an osmate ester by the action of oxone allows the preparation of ketones or carboxylic acids in high yields. This method should be applicable as an alternative to ozonolysis.
B. R. Travis, R. S. Narayan, B. Borhan, J. Am. Chem. Soc., 2002, 124, 3824-3825.

A gold(I)-catalyzed oxidative cleavage of alkenes with tert-butyl hydrogenperoxide (TBHP) as the oxidant in the presence of neocuproine afforded ketones or aldehydes as products.
D. Xing, B. Guan, G. Cai, Z. Fang, L. Yang, Z. Shi, Org. Lett., 2006, 8, 693-696.

Specific oxidation protocols have been developed for the cleavage of styrenes, aliphatic olefins, and terminal aliphatic olefins to carbonyl compounds with ruthenium trichloride as catalyst. Olefins that are not fully substituted are converted to aldehydes rather than carboxylic acids.
D. Yang, C. Zhang, J. Org. Chem., 2001, 66, 4814-4818.

Osmium tetroxide has been microencapsulated in a polyurea matrix. These microcapsules have been effectively used as recyclable catalysts in the dihydroxylation and the oxidative cleavage of olefins.
S. V. Ley, C. Ramarao, A.-L. Lee, N. Ostergaard, S. C. Smith, I. M. Shirley, Org. Lett., 2003, 5, 185-187.

Oxidative ring expansion of methylenecyclopropanes with CAN under oxygen atmosphere was investigated. A facile conversion affording 2,2-diarylcyclobutanones occurred in good yields.
V. Nair, T. D. Suja, K. Mohanan, Synthesis, 2006, 2531-2534.

A practical and environmentally friendly method for the oxidative rearrangement of five- and six-membered cyclic tertiary allylic alcohols to α,β-unsaturated β-disubstituted ketones by IBX in DMSO is described. Several conventional protecting groups (e.g., Ac, MOM, and TBDPS) are tolerated.
M. Shibuya, S. Ito, M. Takahashi, Y. Iwabuchi, Org. Lett., 2004, 6, 4303-4306.

Pd-catalyzed enantioselective diborations of prochiral allenes followed by allylation reactions with primary imines provide vinyl boronates which may be oxidized to give nonracemic Mannich products. Alternatively, enantiomerically enriched homoallylic amine derivatives may be obtained by protonation and Suzuki cross-coupling of the vinyl boronate.
J. D. Sieber, J. P. Morken, J. Am. Chem. Soc., 2006, 128, 74-75.

An efficient method for the oxidation of an olefin to the less substituted carbonyl compound is described. This one pot conversion includes hydroboration with borane dimethyl sulfide (BDMS), followed by oxidation of the resulting alkylboranes with tetrapropylammonium perruthenate (TPAP) and NMO.
M. H. Yates, Tetrahedron Lett., 1997, 38, 2813-2816.