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Enantioselective Aza-Friedel–Crafts Reaction of Indoles and Pyrroles Catalyzed by Chiral C1-Symmetric Bis(phosphoric Acid)
http://hdl.handle.net/2237/0002001527
http://hdl.handle.net/2237/00020015270da7fa59-c978-48f7-891f-ba7b14c54eda
| 名前 / ファイル | ライセンス | アクション |
|---|---|---|
Org_Lett_2020_22_9614.pdf (535 KB)
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| Item type | itemtype_ver1(1) | |||||||||||
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| 公開日 | 2021-10-18 | |||||||||||
| タイトル | ||||||||||||
| タイトル | Enantioselective Aza-Friedel–Crafts Reaction of Indoles and Pyrroles Catalyzed by Chiral C1-Symmetric Bis(phosphoric Acid) | |||||||||||
| 言語 | en | |||||||||||
| 著者 |
Hatano, Manabu
× Hatano, Manabu
× Toh, Kohei
× Ishihara, Kazuaki
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| アクセス権 | ||||||||||||
| アクセス権 | open access | |||||||||||
| アクセス権URI | http://purl.org/coar/access_right/c_abf2 | |||||||||||
| 権利 | ||||||||||||
| 言語 | en | |||||||||||
| 権利情報 | ”This document is the Accepted Manuscript version of a Published Work that appeared in final form in [Organic Letters], copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see [https://pubs.acs.org/articlesonrequest/AOR-8XQ9QN5RTSSSFVDPJ9FY].” | |||||||||||
| 内容記述 | ||||||||||||
| 内容記述タイプ | Abstract | |||||||||||
| 内容記述 | A hydrogen bonding network in chiral Brønsted acid catalysts is important for the construction of a chiral cavity and the enhancement of catalytic activity. In this regard, we developed a highly enantioselective aza-Friedel–Crafts reaction of indoles and pyrroles with acyclic α-ketimino esters in the presence of a chiral C1-symmetric BINOL-derived bis(phosphoric acid) catalyst. The desired alkylation products with chiral quaternary carbon centers were obtained in high yields with high enantioselectivities on up to a 1.2-g scale with 0.2 mol % catalyst loading. Interestingly, the absolute configurations of the products from indoles and pyrroles were opposite even with the use of the same chiral catalyst. Moreover, preliminary mechanistic considerations disclosed that a unique hydrogen bonding network with or without π–π interactions among the catalyst and substrates might partially play a pivotal role. | |||||||||||
| 言語 | en | |||||||||||
| 出版者 | ||||||||||||
| 出版者 | ACS Publications | |||||||||||
| 言語 | en | |||||||||||
| 言語 | ||||||||||||
| 言語 | eng | |||||||||||
| 資源タイプ | ||||||||||||
| 資源タイプresource | http://purl.org/coar/resource_type/c_6501 | |||||||||||
| タイプ | journal article | |||||||||||
| 出版タイプ | ||||||||||||
| 出版タイプ | AM | |||||||||||
| 出版タイプResource | http://purl.org/coar/version/c_ab4af688f83e57aa | |||||||||||
| 関連情報 | ||||||||||||
| 関連タイプ | isVersionOf | |||||||||||
| 識別子タイプ | DOI | |||||||||||
| 関連識別子 | https://doi.org/10.1021/acs.orglett.0c03662 | |||||||||||
| 収録物識別子 | ||||||||||||
| 収録物識別子タイプ | PISSN | |||||||||||
| 収録物識別子 | 1523-7060 | |||||||||||
| 書誌情報 |
en : Organic Letters 巻 22, 号 24, p. 9614-9620, 発行日 2020-12-18 |
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| ファイル公開日 | ||||||||||||
| 日付 | 2021-12-18 | |||||||||||
| 日付タイプ | Available | |||||||||||
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Cite as
Hatano, Manabu, Toh, Kohei, Ishihara, Kazuaki, 2020, Enantioselective Aza-Friedel–Crafts Reaction of Indoles and Pyrroles Catalyzed by Chiral C1-Symmetric Bis(phosphoric Acid): ACS Publications, 9614–9620 p.
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