Fleming-Tamao oxidation
Editor-In-Chief: C. Michael Gibson, M.S., M.D. [1]
Overview
The Fleming-Tamao oxidation is the organic oxidation of alkyl silanes into alcohols with peroxides. The research groups of Fleming and Tamao developed procedures for this reaction in parallel to one another [1]. It is especially useful since it allows alcohols to be masked as much more resilient silanes through a synthesis, before stereospecific removal. The reactions are often grouped together since they are mechanistically similar and perform the same transformation, there is no clear choice between them and it is often decided by trying both. An example of this is shown in a synthesise of two different carbasugars each synthesis using one of the methods.[2] The Fleming reaction has recently been reviewed [3]
References
- ↑ "Oxidative cleavage of the silicon-carbon bond: Development, mechanism, scope, and limitations" by Tamao, K. in "Advances in Silicon Chemistry" (1996), 3, 1-62 CODEN: ADSDEO; ISSN: 1059-4256.
- ↑ Rémy Angelaud, Yannick Landais Tetrahedron Letters Volume 38, Issue 51, 22 December 1997, Pages 8841-8844 doi:10.1016/S0040-4039(97)10388-4
- ↑ Ian Fleming, Rolf Henning, David C. Parker, Howard E. Plaut and Philip E. J. Sanderson, J. Chem. Soc., Perkin Trans. 1, 1995, 317 - 337 doi:10.1039/P19950000317