Direct N‑Me Aziridination of Enones

The first direct general method for N-Me aziridination of electron-deficient olefins, enones, is described using N-methyl-O-tosylhydroxylamine as the aminating agent in the presence of a Cu­(OTf)2 catalyst. The aziridination of vinyl ketones, hitherto unknown for N-Me as well as N-H, has been achiev...

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Bibliographic Details
Published inJournal of organic chemistry Vol. 87; no. 5; pp. 3751 - 3757
Main Authors Jat, Jawahar L, Yadav, Ajay K, Pandey, Chandra Bhan, Chandra, Dinesh, Tiwari, Bhoopendra
Format Journal Article
LanguageEnglish
Published United States American Chemical Society 04.03.2022
Subjects
Alkenes
Aziridines
Catalysis
Ketones
Molecular Structure
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Summary:The first direct general method for N-Me aziridination of electron-deficient olefins, enones, is described using N-methyl-O-tosylhydroxylamine as the aminating agent in the presence of a Cu­(OTf)2 catalyst. The aziridination of vinyl ketones, hitherto unknown for N-Me as well as N-H, has been achieved efficiently. The open-flask reaction is stereospecific, operationally simple, and additive-free. It also efficiently affords N-H aziridinated products under a similar reaction condition.
Bibliography:ObjectType-Article-1
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ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.1c02785