Oxidation of Silyl Enol Ethers Using 2-Sulfonyloxaziridines. Synthesis of α-Siloxy Epoxides and α-Hydroxy Carbonyl Compounds

DOI: 10.1021/jo00381a051

Source and publish data:

Journal of Organic Chemistry p. 954 - 955 (1987)

Update date:2022-08-05

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Authors:

Davis, Franklin A.

Sheppard, Aurelia C.

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Article abstract of DOI:10.1021/jo00381a051

The first isolation and detection of α-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 α-hydroxy carbonyl compounds.

Full text of DOI:10.1021/jo00381a051

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