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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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
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author Curle, Jonathan M.
Perieteanu, Marina C.
Humphreys, Philip G.
Kennedy, Alan R.
Tomkinson, Nicholas C. O.
author_facet Curle, Jonathan M.
Perieteanu, Marina C.
Humphreys, Philip G.
Kennedy, Alan R.
Tomkinson, Nicholas C. O.
author_sort Curle, Jonathan M.
collection PubMed
description [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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spelling pubmed-71469112020-04-13 Alkene Syn- and Anti-Oxyamination with Malonoyl Peroxides Curle, Jonathan M. Perieteanu, Marina C. Humphreys, Philip G. Kennedy, Alan R. Tomkinson, Nicholas C. O. Org Lett [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. American Chemical Society 2020-01-30 2020-02-21 /pmc/articles/PMC7146911/ /pubmed/31999132 http://dx.doi.org/10.1021/acs.orglett.0c00253 Text en Copyright © 2020 American Chemical Society This is an open access article published under a Creative Commons Attribution (CC-BY) License (http://pubs.acs.org/page/policy/authorchoice_ccby_termsofuse.html) , which permits unrestricted use, distribution and reproduction in any medium, provided the author and source are cited.
spellingShingle Curle, Jonathan M.
Perieteanu, Marina C.
Humphreys, Philip G.
Kennedy, Alan R.
Tomkinson, Nicholas C. O.
Alkene Syn- and Anti-Oxyamination with Malonoyl Peroxides
title Alkene Syn- and Anti-Oxyamination with Malonoyl Peroxides
title_full Alkene Syn- and Anti-Oxyamination with Malonoyl Peroxides
title_fullStr Alkene Syn- and Anti-Oxyamination with Malonoyl Peroxides
title_full_unstemmed Alkene Syn- and Anti-Oxyamination with Malonoyl Peroxides
title_short Alkene Syn- and Anti-Oxyamination with Malonoyl Peroxides
title_sort alkene syn- and anti-oxyamination with malonoyl peroxides
url 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
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