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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...

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Autores principales: Miyaji, Ryota, Wada, Yuuki, Matsumoto, Akira, Asano, Keisuke, Matsubara, Seijiro
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2017
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.
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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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