Peracid oxidation of trimethylsilyl enol ethers: A facile α-hydroxylation procedure
✍ Scribed by G.M. Rubottom; M.A. Vazquez; D.R. Pelegrina
- Publisher
- Elsevier Science
- Year
- 1974
- Tongue
- French
- Weight
- 192 KB
- Volume
- 15
- Category
- Article
- ISSN
- 0040-4039
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✦ Synopsis
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)!
📜 SIMILAR VOLUMES
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.
Osmium tetroxide/N-methylmorpholine-N-oxide oxidation of silyl enol ethers, derived from ketones with either kinetic or thermodynamic regiochemical control, produces a-ketols in good to excellent yields. The search for means to introduce hydroxyl functionality adjacent to carbonyl has led to develo