Journal of the American Chemical Society p. 5602 - 5605 (1980)
Update date:2022-08-02
Topics:
Rebek, J.
McCready, R.
A number of α-substituted hydroperoxides were examined for their ability to epoxidize olefins in a stereospecific manner.Hydroperoxy ethers, amines, carbonyl compounds, and nitriles showed this capability.Intramolecular epoxidation was demonstrated in cases where ortho esters of some olefinic alcohols were treated with H2O2, and methyl orthooleate - H2O2 mixtures also epoxidized the internal olefin in an intramolecular reaction.Attempts to generate chiral hydroperoxides for asymmetric epoxidation are described and structural features required for epoxidation reagents are discussed.
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