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Chem Pharm Bull (Tokyo)
; 69(10): 1010-1016, 2021 Oct 01.
Article
in English
| MEDLINE
| ID: mdl-34305073
ABSTRACT
α,ß-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,ß-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.