Hypervalent iodine oxidation of trimethylsilyl enol ethers of ketones: A direct synthesis of α-keto triflates
✍ Scribed by Robert M. Moriarty; W. Ruwan Epa; Raju Penmasta; Alok K. Awasthi
- Publisher
- Elsevier Science
- Year
- 1989
- Tongue
- French
- Weight
- 201 KB
- Volume
- 30
- Category
- Article
- ISSN
- 0040-4039
No coin nor oath required. For personal study only.
✦ Synopsis
a-Trifluoromethanesulfonoxy ketones (a-keto triflates) have been synthesized
under very mild conditions by the reaction of silyl enol ethers of ketones and nimethylsilyl trifluormethanesulfonate/iodosobenzene in dichloromethane.
📜 SIMILAR VOLUMES
The oxidation of trimethylsilyl enol ethers, L, in hexane solution, with s-chloroperbenzoic acid (MCPBA), followed by treatment of the crude reaction mixture with acid or base, affords a general, high yield method for the specific a-hydroxylation of ketones (ie, acyloin, 2, production)(Equation l)!
## Hypervalent iodine oxidation of aryl methyl ketones using two equivalents of iodosobenzene diacetate leads to 1.2-aryl migration followed by solvohyperiodination to yield the corresponding methyl a-methoxyarylacetates.