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Chiral Template-Directed Regio-, Diastereo-, and Enantioselective Photodimerization of an Anthracene Derivative Assisted by Complementary Amidinium–Carboxylate Salt Bridge Formation
http://hdl.handle.net/2237/00027920
http://hdl.handle.net/2237/00027920017c4417-e634-42e1-9370-e331b1abc6a0
| 名前 / ファイル | ライセンス | アクション |
|---|---|---|
Yashima_rev (4.4 MB)
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| Item type | 学術雑誌論文 / Journal Article(1) | |||||
|---|---|---|---|---|---|---|
| 公開日 | 2018-04-18 | |||||
| タイトル | ||||||
| タイトル | Chiral Template-Directed Regio-, Diastereo-, and Enantioselective Photodimerization of an Anthracene Derivative Assisted by Complementary Amidinium–Carboxylate Salt Bridge Formation | |||||
| 言語 | en | |||||
| 著者 |
Tanabe, Junki
× Tanabe, Junki× Taura, Daisuke× Ousaka, Naoki× Yashima, Eiji |
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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 [Journal of the American Chemical Society], copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see [http://pubs.acs.org/articlesonrequest/AOR-FIZ9qCwueg6mpxPjheCr].” | |||||
| 抄録 | ||||||
| 内容記述タイプ | Abstract | |||||
| 内容記述 | A series of optically active amidine dimers composed of m-terphenyl backbones joined by a variety of linkers, such as achiral and chiral p-phenylene and chiral amide linkers, were synthesized and used as templates for the regio- (head-to-tail (HT) or head-to-head (HH)), diastereo- (anti or syn), and enantioselective [4 + 4] photocyclodimerization of an achiral m-terphenyl-based carboxylic acid monomer bearing a prochiral 2-substituted anthracene at one end (1) through complementary amidinium–carboxylate salt bridges. The amidine dimers linked by p-phenylene linkages almost exclusively afforded the chiral syn-HT and anti-HH dimers at 25 °C, while those joined by amide linkers produced all four dimers. The p-phenylene-linked templates tended to enhance the syn-HT-photodimer formation at high temperatures with no significant changes in the product enantiomeric excess (ee), while the anti-HH-photodimer formation remarkably increased with the decreasing temperature accompanied by a significant enhancement of the product ee up to −86% at −50 °C. Temperature-dependent inversion of the chirality of the anti-HH dimer was observed when the chiral phenylene-linked amidine dimer was used and the product ee was changed from 22% at 50 °C to −86% at −50 °C. A similar enhancement of the enantioselectivity of the anti-HH dimer was also observed for the chiral amide-linked template, producing the anti-HH dimer with up to −88% ee at −50 °C. The observed difference in the regio-, diastereo-, and enantioselectivities due to the difference in the linker structures of the amidine dimers during the template-directed photodimerization of 1 was discussed on the basis of a reversible conformational change in the amidine dimers complexed with 1. | |||||
| 言語 | en | |||||
| 内容記述 | ||||||
| 内容記述タイプ | Other | |||||
| 内容記述 | ファイル公開日: 2018/05/09 | |||||
| 言語 | ja | |||||
| 内容記述 | ||||||
| 内容記述タイプ | Other | |||||
| 内容記述 | Publication Date (Web): May 9, 2017 | |||||
| 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 | |||||
| DOI | ||||||
| 関連タイプ | isVersionOf | |||||
| 識別子タイプ | DOI | |||||
| 関連識別子 | https://doi.org/10.1021/jacs.7b03317 | |||||
| ISSN | ||||||
| 収録物識別子タイプ | PISSN | |||||
| 収録物識別子 | 0002-7863 | |||||
| 書誌情報 |
en : Journal of the American Chemical Society 巻 139, 号 21, p. 7388-7398, 発行日 2017-05-31 |
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| 著者版フラグ | ||||||
| 値 | author | |||||
