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Dynamic parallel kinetic resolution of α-ferrocenyl cation initiated by chiral Brønsted acid catalyst
https://iwate-u.repo.nii.ac.jp/records/15787
https://iwate-u.repo.nii.ac.jp/records/15787007f85ab-25b2-4a8a-a1a6-a3070e78be95
| 名前 / ファイル | ライセンス | アクション |
|---|---|---|
cs-v12n30p10306-10312 (1.1 MB)
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| Item type | 学術雑誌論文 / Journal Article(1) | |||||
|---|---|---|---|---|---|---|
| 公開日 | 2022-09-12 | |||||
| タイトル | ||||||
| タイトル | Dynamic parallel kinetic resolution of α-ferrocenyl cation initiated by chiral Brønsted acid catalyst | |||||
| 言語 | ||||||
| 言語 | eng | |||||
| 資源タイプ | ||||||
| 資源タイプ識別子 | http://purl.org/coar/resource_type/c_6501 | |||||
| 資源タイプ | journal article | |||||
| 著者 |
TODA, Yasunori
× TODA, Yasunori× KORENAGA, Toshinobu× OBAYASHI, Ren× KIKUCHI, Jun× TERADA, Masahiro |
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| 著者(機関) | ||||||
| 値 | Department of Chemistry, Graduate School of Science, Tohoku University | |||||
| 著者(機関) | ||||||
| 値 | Department of Chemistry and Biological Sciences, Faculty of Science and Engineering, Iwate University | |||||
| 著者(機関) | ||||||
| 値 | Department of Chemistry, Graduate School of Science, Tohoku University | |||||
| 著者(機関) | ||||||
| 値 | Department of Chemistry, Graduate School of Science, Tohoku University | |||||
| 著者(機関) | ||||||
| 値 | Department of Chemistry, Graduate School of Science, Tohoku University | |||||
| 登録日 | ||||||
| 日付 | 2022-09-12 | |||||
| 書誌情報 |
Chemical Science 巻 12, 号 30, p. 10306-10312, 発行日 2021-06-29 |
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| ISSN | ||||||
| 収録物識別子タイプ | ISSN | |||||
| 収録物識別子 | 20416520 | |||||
| 抄録 | ||||||
| 内容記述タイプ | Abstract | |||||
| 内容記述 | The dynamic parallel kinetic resolution (DPKR) of an α-ferrocenyl cation intermediate under the influence of a chiral conjugate base of a chiral phosphoric acid catalyst has been demonstrated in an SN1 type substitution reaction of a racemic ferrocenyl derivative with a nitrogen nucleophile. The present method provides efficient access to a ferrocenylethylamine derivative in a highly enantioselective manner, which is potentially useful as a key precursor of chiral ligands for metal catalysis. The mechanism of the present intriguing resolution system was elucidated by control experiments using the enantio-pure precursor of relevant α-ferrocenyl cation intermediates and the hydroamination of vinylferrocene. Further theoretical studies enabled the elucidation of the origin of the stereochemical outcome as well as the efficient DPKR. The present DPKR, which opens a new frontier for kinetic resolution, involves the racemization process through the formation of vinylferrocene and the chemo-divergent parallel kinetic resolution of the enantiomeric α-ferrocenyl cations generated by the protonation/deprotonation sequence of vinylferrocene. | |||||
| 抄録（URL） | ||||||
| 表示名 | Dynamic parallel kinetic resolution of α-ferrocenyl cation initiated by chiral Brønsted acid catalyst | |||||
| URL | https://pubs.rsc.org/en/content/articlelanding/2021/SC/D1SC02122B | |||||
| 出版者 | ||||||
| 出版者 | The Royal Society of Chemistry | |||||
| 権利 | ||||||
| 権利情報 | © 2021 The Author(s). | |||||
| 権利URI | ||||||
| 権利情報 | https://creativecommons.org/licenses/by-nc/3.0/ | |||||
| DOI | ||||||
| 関連タイプ | isIdenticalTo | |||||
| 識別子タイプ | DOI | |||||
| 関連識別子 | info:doi/10.1039/d1sc02122b | |||||
| 著者版フラグ | ||||||
| 出版タイプ | VoR | |||||
| 出版タイプResource | http://purl.org/coar/version/c_970fb48d4fbd8a85 | |||||
