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Synlett 2007(20): 3226-3227  
DOI: 10.1055/s-2007-990918
SPOTLIGHT
© Georg Thieme Verlag Stuttgart · New York

Methy(trifluoromethyl)dioxirane (TFD): A Powerful and Versatile Oxidant in Organic Synthesis

Xu-Ye Tao*
The College of Chemistry & Material Science, Hebei Normal University, Shijiazhuang 050016, P. R. of China
e-Mail: taoxychem@sina.com.cn;
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Publication History

Publication Date:
03 December 2007 (online)

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Introduction

During the last two decades, the use of dioxiranes as oxidants in organic synthesis has increased considerably. [1] Methyl(trifluoromethyl)dioxirane (TFD) has the highest reactivity among dioxiranes reported so far, and has been utilized for a broad variety of oxidative transformations in organic synthesis. Exemplary transformations are the monohydroxylation of alkanes, [2] chemoselective oxidation of allylic alcohols, [3] optically active sec,sec-1,2-diols [4] and simple sulfides, [5] oxyfunctionalization of unactivated tertiary and secondary C-H bonds of alkylamines [6] and aliphatic­ esters, [7] epoxidation of primary and secondary alkenylammonium salts [8] and chiral camphor N-enoylpyrazolidinones, [9] oxidative cleavage of acetals, ketals [10] and aryl oxazolines, [11] and conversion of cyclic ethers into lactones. [10] It is also found to be a useful reagent for the oxyfunctionalization of natural [12-14] and non-natural [15-19] targets, which include the direct hydroxylation at the side-chain C-25 of cholestane derivatives and vitamin D3 Windaus-Grundmann ketone, [12] high stereo- and regioselective conversion of vitamin D2 into its (all-R) tetraepoxide and C-25 hydroxy derivative, [13] stereoselective synthesis of (all-R)-vitamin D3 triepoxide and its 25-hydroxy derivative, [14] oxidation of centropolyindans, [15] buckminsterfullerene C60, [16] Binor S, [17] hydrocarbons bearing cyclopropyl moieties, [18] and selective bridgehead dihydroxylation of fenestrindane. [19]