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...
| Main Authors: | , , , , |
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| Format: | Article |
| Language: | English |
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Beilstein-Institut
2017-08-01
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| Series: | Beilstein Journal of Organic Chemistry |
| Subjects: | |
| Online Access: | https://doi.org/10.3762/bjoc.13.151 |
| _version_ | 1829530521246367744 |
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| author | Ryota Miyaji Yuuki Wada Akira Matsumoto Keisuke Asano Seijiro Matsubara |
| author_facet | Ryota Miyaji Yuuki Wada Akira Matsumoto Keisuke Asano Seijiro Matsubara |
| author_sort | Ryota Miyaji |
| collection | DOAJ |
| 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. |
| first_indexed | 2024-12-16T18:05:09Z |
| format | Article |
| id | doaj.art-0d5c741ac5e346d498795c2d5f200874 |
| institution | Directory Open Access Journal |
| issn | 1860-5397 |
| language | English |
| last_indexed | 2024-12-16T18:05:09Z |
| publishDate | 2017-08-01 |
| publisher | Beilstein-Institut |
| record_format | Article |
| series | Beilstein Journal of Organic Chemistry |
| spelling | doaj.art-0d5c741ac5e346d498795c2d5f2008742022-12-21T22:21:56ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972017-08-011311518152310.3762/bjoc.13.1511860-5397-13-151Bifunctional organocatalysts for the asymmetric synthesis of axially chiral benzamidesRyota Miyaji0Yuuki Wada1Akira Matsumoto2Keisuke Asano3Seijiro Matsubara4Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Kyotodaigaku-Katsura, Nishikyo, Kyoto 615-8510, JapanDepartment of Material Chemistry, Graduate School of Engineering, Kyoto University, Kyotodaigaku-Katsura, Nishikyo, Kyoto 615-8510, JapanDepartment of Material Chemistry, Graduate School of Engineering, Kyoto University, Kyotodaigaku-Katsura, Nishikyo, Kyoto 615-8510, JapanDepartment of Material Chemistry, Graduate School of Engineering, Kyoto University, Kyotodaigaku-Katsura, Nishikyo, Kyoto 615-8510, JapanDepartment of Material Chemistry, Graduate School of Engineering, Kyoto University, Kyotodaigaku-Katsura, Nishikyo, Kyoto 615-8510, JapanBifunctional 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.https://doi.org/10.3762/bjoc.13.151axial chiralitybenzamidebifunctional organocatalystmolecular conformationmultipoint recognition |
| spellingShingle | Ryota Miyaji Yuuki Wada Akira Matsumoto Keisuke Asano Seijiro Matsubara Bifunctional organocatalysts for the asymmetric synthesis of axially chiral benzamides Beilstein Journal of Organic Chemistry axial chirality benzamide bifunctional organocatalyst molecular conformation multipoint recognition |
| 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 | axial chirality benzamide bifunctional organocatalyst molecular conformation multipoint recognition |
| url | https://doi.org/10.3762/bjoc.13.151 |
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