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Cascade radical reaction of substrates with a carbon–carbon triple bond as a radical acceptor

The limitation of hydroxamate ester as a chiral Lewis acid coordination moiety was first shown in an intermolecular reaction involving a radical addition and sequential allylation processes. Next, the effect of hydroxamate ester was studied in the cascade addition–cyclization–trapping reaction of su...

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Autores principales: Miyabe, Hideto, Asada, Ryuta, Takemoto, Yoshiji
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2013
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3701377/
https://www.ncbi.nlm.nih.gov/pubmed/23843907
http://dx.doi.org/10.3762/bjoc.9.128
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author Miyabe, Hideto
Asada, Ryuta
Takemoto, Yoshiji
author_facet Miyabe, Hideto
Asada, Ryuta
Takemoto, Yoshiji
author_sort Miyabe, Hideto
collection PubMed
description The limitation of hydroxamate ester as a chiral Lewis acid coordination moiety was first shown in an intermolecular reaction involving a radical addition and sequential allylation processes. Next, the effect of hydroxamate ester was studied in the cascade addition–cyclization–trapping reaction of substrates with a carbon–carbon triple bond as a radical acceptor. When substrates with a methacryloyl moiety and a carbon–carbon triple bond as two polarity-different radical acceptors were employed, the cascade reaction proceeded effectively. A high level of enantioselectivity was also obtained by a proper combination of chiral Lewis acid and these substrates.
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spelling pubmed-37013772013-07-10 Cascade radical reaction of substrates with a carbon–carbon triple bond as a radical acceptor Miyabe, Hideto Asada, Ryuta Takemoto, Yoshiji Beilstein J Org Chem Full Research Paper The limitation of hydroxamate ester as a chiral Lewis acid coordination moiety was first shown in an intermolecular reaction involving a radical addition and sequential allylation processes. Next, the effect of hydroxamate ester was studied in the cascade addition–cyclization–trapping reaction of substrates with a carbon–carbon triple bond as a radical acceptor. When substrates with a methacryloyl moiety and a carbon–carbon triple bond as two polarity-different radical acceptors were employed, the cascade reaction proceeded effectively. A high level of enantioselectivity was also obtained by a proper combination of chiral Lewis acid and these substrates. Beilstein-Institut 2013-06-13 /pmc/articles/PMC3701377/ /pubmed/23843907 http://dx.doi.org/10.3762/bjoc.9.128 Text en Copyright © 2013, Miyabe et al. https://creativecommons.org/licenses/by/2.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Full Research Paper
Miyabe, Hideto
Asada, Ryuta
Takemoto, Yoshiji
Cascade radical reaction of substrates with a carbon–carbon triple bond as a radical acceptor
title Cascade radical reaction of substrates with a carbon–carbon triple bond as a radical acceptor
title_full Cascade radical reaction of substrates with a carbon–carbon triple bond as a radical acceptor
title_fullStr Cascade radical reaction of substrates with a carbon–carbon triple bond as a radical acceptor
title_full_unstemmed Cascade radical reaction of substrates with a carbon–carbon triple bond as a radical acceptor
title_short Cascade radical reaction of substrates with a carbon–carbon triple bond as a radical acceptor
title_sort cascade radical reaction of substrates with a carbon–carbon triple bond as a radical acceptor
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3701377/
https://www.ncbi.nlm.nih.gov/pubmed/23843907
http://dx.doi.org/10.3762/bjoc.9.128
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