Oxidation of Silyl Enol Ethers Using 2-sulfonyloxaziridines. Synthesis of A-siloxy Epoxides and α-hydroxy Carbonyl Compounds

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Abstract

The first isolation and detection of a-siloxy epoxides 2 in the oxidation of silyl enol ethers 1 to α-hydroxy carbonyl compounds 4 (Rubottom reaction) by 2-sulfonyloxaziridine 5 is described. Asymmetric oxidation of silyl enol ethers by (+)-(R,R)-6 affords optically active a-hydroxy carbonyl compounds. © 1987, American Chemical Society. All rights reserved.

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Davis, F. A., & Sheppard, A. C. (1987). Oxidation of Silyl Enol Ethers Using 2-sulfonyloxaziridines. Synthesis of A-siloxy Epoxides and α-hydroxy Carbonyl Compounds. Journal of Organic Chemistry, 52(5), 954–955. https://doi.org/10.1021/jo00381a051

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