Categories: C=O Bond Formation > Synthesis of carboxylic acids >
Synthesis of carboxylic acids 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.
An efficient method for the oxidative cleavage of internal and terminal
alkynes to carboxylic acids using a combination of RuO2/Oxone/NaHCO3
in a CH3CN/H2O/EtOAc solvent system is described.
Various alkynes, regardless of their electron density, were oxidized to
carboxylic acids in excellent yield.
D. Yang, F. Chen, Z.-M. Dong, D.-W. Zhang, J. Org. Chem., 2004,
69, 209-212.
A highly
enantioselective and catalytic vinylation of aldehydes leads to allylic alcohols
that are then transformed to the allylic amines via Overman's [3,3]-sigmatropic
rearrangement of imidates. Oxidative cleavage of the allylic amines furnishes amino acids in good yields and excellent ee's. The scope and utility of this
method are demonstrated by the synthesis of challenging allylic amines and their
subsequent transformation to valuable nonproteinogenic amino acids, including
both D and L configured (1-adamantyl)glycine.
Y. K. Chen. A. E. Lurain, P. J. Walsh, J. Am. Chem. Soc., 2002, 124, 12225-12231.
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.
