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Electrophilic Epoxidation of α,β-Unsaturated Oximes with Dioxiranes and Ring Opening of the Epoxides
Chemical & Pharmaceutical Bulletin  (IF1.645),  Pub Date : 2021-10-01, DOI: 10.1248/cpb.c21-00533
Miyu Furugoori, Kiwamu Yoshida, Yoshimitsu Hashimoto, Nobuyoshi Morita, Kosaku Tanaka, III, Osamu Tamura

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.

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