Electrophilic Epoxidation of α,β-Unsaturated Oximes with Dioxiranes and Ring Opening of the Epoxides.

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 enantioselectivity.

Citation

Miyu Furugoori, Kiwamu Yoshida, Yoshimitsu Hashimoto, Nobuyoshi Morita, Kosaku Tanaka Iii, Osamu Tamura. Electrophilic Epoxidation of α,β-Unsaturated Oximes with Dioxiranes and Ring Opening of the Epoxides. Chemical & pharmaceutical bulletin. 2021 Oct 01;69(10):1010-1016

PMID: 34305073

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