Hydroxylation of Carbonyl Compounds via Silyl Enol Ethers

Alfred Hassner, Robert H. Reuss, Harold W. Pinnick

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Silyl enol ethers 1, which are readily available from the corresponding aldehydes, react rapidly with m-chloroperbenzoic acid to afford the protected α-hydroxy aldehydes 3 in good yield. Treatment of 3 with acetic anhydride and triethylamine produces -acetoxy aldehydes 5. This sequence provides a simple procedure for α-hydroxylation of aldehydes. Silyl enol ethers of ketones 10 are converted directly to α-siloxy ketones 11 with m-chloroperbenzoic acid representing a significant improvement over the usual enol ether or acetate procedure.

Original languageEnglish
Pages (from-to)3427-3429
Number of pages3
JournalJournal of Organic Chemistry
Issue number23
StatePublished - 1 Nov 1975
Externally publishedYes


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