Synthetic methods. VIII. Hydroxylation of carbonyl compounds via silyl enol ethers

A Hassner, RH Reuss, HW Pinnick

文献索引：Hassner,A. et al. Journal of Organic Chemistry, 1975 , vol. 40, # 23 p. 3427 - 3429

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被引用次数: 133

摘要

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