Showa Pharmaceutical University.
Chem Pharm Bull (Tokyo). 2021 Oct 1;69(10):1010-1016. doi: 10.1248/cpb.c21-00533. Epub 2021 Jul 21.
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.
α,β-不饱和肟在原位生成的二甲双氧化进行亲电环氧化反应，以良好的收率得到相应的环氧化物。该反应是通过将α,β-不饱和酮转化为其肟来实现“羰基反转”的一个例子。环氧化物的亲核开环反应得到了α-取代产物。Shi 不对称环氧化肟反应具有中等的对映选择性。
