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  1. B200 工学部/工学研究科
  2. B200a 雑誌掲載論文
  3. 学術雑誌

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/2237/00027920
017c4417-e634-42e1-9370-e331b1abc6a0
名前 / ファイル ライセンス アクション
Yashima_rev.pdf Yashima_rev (4.4 MB)
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

WEKO 76182

en Tanabe, Junki

Search repository
Taura, Daisuke

× Taura, Daisuke

WEKO 76183

en Taura, Daisuke

Search repository
Ousaka, Naoki

× Ousaka, Naoki

WEKO 76184

en Ousaka, Naoki

Search repository
Yashima, Eiji

× Yashima, Eiji

WEKO 76185

en Yashima, Eiji

Search repository
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 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
内容記述タイプ Abstract
内容記述
内容記述 ファイル公開日: 2018/05/09
言語 ja
内容記述タイプ Other
内容記述
内容記述 Publication Date (Web): May 9, 2017
言語 en
内容記述タイプ Other
出版者
言語 en
出版者 ACS Publications
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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