Alkene Syn- and Anti-Oxyamination with Malonoyl Peroxides

[Image: see text] Malonoyl peroxide 6 is an effective reagent for the syn- or anti-oxyamination of alkenes. Reaction of 6 and an alkene in the presence of O-tert-butyl-N-tosylcarbamate (R(3) = CO(2)(t)Bu) leads to the anti-oxyaminated product in up to 99% yield. Use of O-methyl-N-tosyl carbamate (R(...

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Detalles Bibliográficos
Autores principales: Curle, Jonathan M., Perieteanu, Marina C., Humphreys, Philip G., Kennedy, Alan R., Tomkinson, Nicholas C. O.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2020
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7146911/
https://www.ncbi.nlm.nih.gov/pubmed/31999132
http://dx.doi.org/10.1021/acs.orglett.0c00253
Descripción
Sumario:[Image: see text] Malonoyl peroxide 6 is an effective reagent for the syn- or anti-oxyamination of alkenes. Reaction of 6 and an alkene in the presence of O-tert-butyl-N-tosylcarbamate (R(3) = CO(2)(t)Bu) leads to the anti-oxyaminated product in up to 99% yield. Use of O-methyl-N-tosyl carbamate (R(3) = CO(2)Me) as the nitrogen nucleophile followed by treatment of the product with trifluoroacetic acid leads to the syn-oxyaminated product in up to 77% yield. Mechanisms consistent with the observed selectivities are proposed.

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