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I2-Catalyzed Regioselective Oxo- and Hydroxy-acyloxylation of Alkenes and Enol Ethers: A Facile Access to α-Acyloxyketones, Esters, and Diol Derivatives

Rambabu N. Reddi, Pragati K. Prasad and Arumugam Sudalai*

*Chemical Engineering and Process Development Division, National Chemical Laboratory, Pashan Road, Pune, 411008, India, Email: a.sudalaincl.res.in

R. N. Reddi, P. K. Prasad, A. Sudalai, Org. Lett., 2014, 16, 5674-5677.

DOI: 10.1021/ol5027393 (free Supporting Information)


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Abstract

I2-catalyzed oxo-acyloxylation of alkenes and enol ethers with carboxylic acids provides α-acyloxyketones and esters in high yields. This unprecedented regioselective oxidative process employs TBHP and Et3N in stoichiometric amounts under metal-free conditions in DMSO as solvent. α-Acyloxyketones can be converted in situ to monoprotected diol derivatives in excellent yields upon treatment with BH3ĚSMe2.

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Key Words

Hydroxyketones, Diols, TBHP, Borane


ID: J54-Y2014