Olefin oxidative cleavage and dioxetane formation using triethylsilyl hydrotrioxide: Applications to preparation of potent antimalarial 1,2,4-trioxanes
✍ Scribed by Gary H. Posner; Chang Ho Oh; Wilbur K. Milhous
- Book ID
- 104225131
- Publisher
- Elsevier Science
- Year
- 1991
- Tongue
- French
- Weight
- 316 KB
- Volume
- 32
- Category
- Article
- ISSN
- 0040-4039
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✦ Synopsis
Oxidative cleavage of alkenyl esters and ethers using Et$iOOOH was found to be easier than oxidative cleavage of hydrocarbon alkenes, and Et3SiOOOH was successfully applied to very short syntheses of new, simple, and potent antimalarial trioxanes 6 and 8.
We have reported recently that triethylsilyl hydrotrioxide (Et$iOOOH), prepared in situ at -78'C in CH2Cl2 solution from triethylsilane plus ozone, is an effective new oxidizing reagent (1) that oxidatively cleaves unactivated terminal and internal alkenes into carbonyl fragments and (2) that forms 1,2-dioxetanes from vinyl aromatics and from vinyl ethers directly without the intermediacy of free 102.1 Now at Johns Hopkins we have discovered, and report herein, some subtle aspects of the oxidative cleavage process and some valuable applications