Fleming -Kumada oxidation

Stereoselective oxidation of alkyl-silanes into the corresponding alkyl-alcohols using peracids. 

Name Reactions A Collection of Detailed Mechanisms and Synthetic Applications, DOI 10.1007/978-3-319-03979-4 108, Springer International Publishing Switzerland 2014 

Mullins, R. J. Jolley, S. L. Knapp, A. R. Tamao-Kumada-Fleming Oxidation. In Name Reactions for Functional Group Transformations, Li, J. J., Ed. Wiley Hoboken, NJ, 2007, pp T31-1A1. (Review). 

Name Reactions, 4th ed., DOI 10.1007/978-3-642-01053-8 100, Springer-Verlag Berlin Heidelberg 2009 

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Oxidation of alkyl fluorosilanes to the corresponding alcohols. A variant of the Fleming-Kumada oxidation. 

This reaction, depending on the details of the reaction, is known as the Fleming Oxidation, the Fleming-Tamao Oxidation, the Tamao-Fleming Oxidation, or the Tamao-Kumada Oxidation. 

Until recently, little attention has been paid to the synthetic potential of this oxidative cleavage. Due largely to the studies of Tamao and Kumada and, independendy, those of Fleming, and dieir coworkers, such potendal has now been revealed. It is the purpose of this ch ter to highlight some of its appli-cadons. Since the emphasis is on synthetic utility, only high-yielding reactions have been selected for inclusion. Unless otherwise stated, 1 compounds shown are racemic only one enantiomer is shown for clarity. 

The Tamao-Kumada and Fleming oxidation reactions involve the oxidation of specific silyl groups to provide a hydroxyl group with retention of configuration.1... 

The Tamao-Kumada and Fleming oxidations have found wide synthetic utility in the oxidation of a variety of silyl groups.6,26 29 However, the true virtue of these reactions lies in the manner in which the silyl group is introduced into the molecule to be oxidized. A number of creative strategies have been developed for this process, some of which will be highlighted below. 

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