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Bifunctional organocatalysts for the asymmetric synthesis of axially chiral benzamides
Bifunctional organocatalysts bearing amino and urea functional groups in a chiral molecular skeleton were applied to the enantioselective synthesis of axially chiral benzamides via aromatic electrophilic bromination. The results demonstrate the versatility of bifunctional organocatalysts for the ena...
Autores principales: | , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
Beilstein-Institut
2017
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5550815/ https://www.ncbi.nlm.nih.gov/pubmed/28845196 http://dx.doi.org/10.3762/bjoc.13.151 |
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author | Miyaji, Ryota Wada, Yuuki Matsumoto, Akira Asano, Keisuke Matsubara, Seijiro |
author_facet | Miyaji, Ryota Wada, Yuuki Matsumoto, Akira Asano, Keisuke Matsubara, Seijiro |
author_sort | Miyaji, Ryota |
collection | PubMed |
description | Bifunctional organocatalysts bearing amino and urea functional groups in a chiral molecular skeleton were applied to the enantioselective synthesis of axially chiral benzamides via aromatic electrophilic bromination. The results demonstrate the versatility of bifunctional organocatalysts for the enantioselective construction of axially chiral compounds. Moderate to good enantioselectivities were afforded with a range of benzamide substrates. Mechanistic investigations were also carried out. |
format | Online Article Text |
id | pubmed-5550815 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2017 |
publisher | Beilstein-Institut |
record_format | MEDLINE/PubMed |
spelling | pubmed-55508152017-08-25 Bifunctional organocatalysts for the asymmetric synthesis of axially chiral benzamides Miyaji, Ryota Wada, Yuuki Matsumoto, Akira Asano, Keisuke Matsubara, Seijiro Beilstein J Org Chem Full Research Paper Bifunctional organocatalysts bearing amino and urea functional groups in a chiral molecular skeleton were applied to the enantioselective synthesis of axially chiral benzamides via aromatic electrophilic bromination. The results demonstrate the versatility of bifunctional organocatalysts for the enantioselective construction of axially chiral compounds. Moderate to good enantioselectivities were afforded with a range of benzamide substrates. Mechanistic investigations were also carried out. Beilstein-Institut 2017-08-02 /pmc/articles/PMC5550815/ /pubmed/28845196 http://dx.doi.org/10.3762/bjoc.13.151 Text en Copyright © 2017, Miyaji et al. https://creativecommons.org/licenses/by/4.0https://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/4.0), 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 Miyaji, Ryota Wada, Yuuki Matsumoto, Akira Asano, Keisuke Matsubara, Seijiro Bifunctional organocatalysts for the asymmetric synthesis of axially chiral benzamides |
title | Bifunctional organocatalysts for the asymmetric synthesis of axially chiral benzamides |
title_full | Bifunctional organocatalysts for the asymmetric synthesis of axially chiral benzamides |
title_fullStr | Bifunctional organocatalysts for the asymmetric synthesis of axially chiral benzamides |
title_full_unstemmed | Bifunctional organocatalysts for the asymmetric synthesis of axially chiral benzamides |
title_short | Bifunctional organocatalysts for the asymmetric synthesis of axially chiral benzamides |
title_sort | bifunctional organocatalysts for the asymmetric synthesis of axially chiral benzamides |
topic | Full Research Paper |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5550815/ https://www.ncbi.nlm.nih.gov/pubmed/28845196 http://dx.doi.org/10.3762/bjoc.13.151 |
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