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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...
Autores principales: | , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
Beilstein-Institut
2013
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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. |
format | Online Article Text |
id | pubmed-3701377 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2013 |
publisher | Beilstein-Institut |
record_format | MEDLINE/PubMed |
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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