| Item type |
itemtype_ver1(1) |
| 公開日 |
2021-10-18 |
| タイトル |
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タイトル |
Enantioselective Aza-Friedel–Crafts Reaction of Indoles and Pyrroles Catalyzed by Chiral C1-Symmetric Bis(phosphoric Acid) |
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言語 |
en |
| 著者 |
Hatano, Manabu
Toh, Kohei
Ishihara, Kazuaki
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| アクセス権 |
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|
アクセス権 |
open access |
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アクセス権URI |
http://purl.org/coar/access_right/c_abf2 |
| 権利 |
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|
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 |
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内容記述タイプ |
Abstract |
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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 |
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出版者 |
ACS Publications |
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言語 |
en |
| 言語 |
|
|
言語 |
eng |
| 資源タイプ |
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資源タイプ識別子 |
http://purl.org/coar/resource_type/c_6501 |
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資源タイプ |
journal article |
| 出版タイプ |
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|
出版タイプ |
AM |
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出版タイプResource |
http://purl.org/coar/version/c_ab4af688f83e57aa |
| 関連情報 |
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|
関連タイプ |
isVersionOf |
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|
識別子タイプ |
DOI |
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関連識別子 |
https://doi.org/10.1021/acs.orglett.0c03662 |
| 収録物識別子 |
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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 |
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|
日付 |
2021-12-18 |
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日付タイプ |
Available |
Org_Lett_2020_22_9614.pdf (535 KB)
