Electrophilic Epoxidation of α,β-Unsaturated Oximes with Dioxiranes and Ring Opening of the Epoxides
Electrophilic Epoxidation of α,β-Unsaturated Oximes with Dioxiranes and Ring Opening of the Epoxides
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DOI：
10.1248/cpb.c21-00533
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发表时间：
2021-10-01
影响因子：
1.7
通讯作者：
Tamura, Osamu
中科院分区：
文献类型：
--
作者：
Furugoori, Miyu;Yoshida, Kiwamu;Tamura, Osamu
α，β-不饱和肟与原位生成的二甲基二环氧乙烷发生亲电环氧化反应，以较好的产率得到相应的环氧化物。该反应是通过将α，β-不饱和酮转化为它们的肟的“羰基聚合”的一个实例。环氧化物的亲核开环反应提供α，-取代的产物。肟的不对称环氧化反应具有中等的对映选择性。
alpha,beta-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 alpha,beta-unsaturated ketones to their oximes. Nucleophilic ring-opening reactions of the epoxides afforded alpha,-substituted products. Shi asymmetric epoxidation of the oximes proceeded with moderate enantioselectivity.