Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
Electrophilic epoxidation of α,β-unsaturated oximes with dioxiranes and ring opening of the epoxides
Miyu FurugooriKiwamu YoshidaYoshimitsu HashimotoNobuyoshi MoritaKosaku TanakaOsamu Tamura
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ジャーナル フリー 早期公開

論文ID: c21-00533

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α,β-Unsaturated oximes underwent electrophilic epoxidation with in-situ-generated dimethyldioxirane to give the corresponding epoxides in good yields. This reaction is an example of “carbonyl umpolung” by transformation of α,β-unsaturated ketones to their oximes. Nucleophilic ring-opening reactions of the epoxides afforded α-substituted products. Shi asymmetric epoxidation of the oximes proceeded with moderate asymmetric selectivity.

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