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Catalytic Enantioselective Construction of Decalin Derivatives by Dynamic Kinetic Desymmetrization of C2-Symmetric Derivatives through Aldol–Aldol Annulation
https://oist.repo.nii.ac.jp/records/2665
https://oist.repo.nii.ac.jp/records/2665f7eaccb5-e7d5-4f71-aca6-6152ec399c71
名前 / ファイル | ライセンス | アクション |
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JOC decalin mechanism 220517 (1) (2.0 MB)
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Item type | 学術雑誌論文 / Journal Article(1) | |||||
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公開日 | 2022-06-20 | |||||
タイトル | ||||||
言語 | en | |||||
タイトル | Catalytic Enantioselective Construction of Decalin Derivatives by Dynamic Kinetic Desymmetrization of C2-Symmetric Derivatives through Aldol–Aldol Annulation | |||||
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(英) |
Aher, Ravindra D.
× Aher, Ravindra D.× Ishikawa, Atsuhiro× Yamanaka, Masahiro× Tanaka, Fujie |
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書誌情報 |
en : The Journal of Organic Chemistry 巻 87, 号 12, p. 8151-8157, 発行日 2022-06-06 |
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抄録 | ||||||
内容記述タイプ | Other | |||||
内容記述 | We have developed and investigated a catalytic desymmetrization reaction strategy that affords functionalized decalin derivatives with high enantioselectivities from C2-symmetric derivatives through aldol–aldol annulation. We identified the structural moieties of the catalyst necessary for the formation of the decalin derivative with high enantioselectivity. We elucidated the mechanisms of the catalyzed reactions: the first aldol reaction step was reversible, and the second aldol step was rate-limiting and stereochemistry-determining and was enantioselective. Using theoretical calculations guided by the experimental results, we identified the interactions between the catalyst and the transition state that led to the major enantiomer. The information obtained in this study will be useful for the development of catalysts and chemical transformations. | |||||
出版者 | ||||||
出版者 | American Chemical Society | |||||
ISSN | ||||||
収録物識別子タイプ | ISSN | |||||
収録物識別子 | 0022-3263 | |||||
ISSN | ||||||
収録物識別子タイプ | ISSN | |||||
収録物識別子 | 1520-6904 | |||||
PubMed番号 | ||||||
関連タイプ | isVersionOf | |||||
識別子タイプ | PMID | |||||
関連識別子 | info:pmid/35666096 | |||||
DOI | ||||||
関連タイプ | isVersionOf | |||||
識別子タイプ | DOI | |||||
関連識別子 | info:doi/10.1021/acs.joc.2c00889 | |||||
権利 | ||||||
権利情報 | © 2022 American Chemical Society | |||||
権利 | ||||||
権利情報 | This document is the Accepted Manuscript version of a Published Work that appeared in final form in The Journal of Organic Chemistry, copyright © 2022 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/doi/10.1021/acs.joc.2c00889. | |||||
関連サイト | ||||||
識別子タイプ | URI | |||||
関連識別子 | https://pubs.acs.org/doi/10.1021/acs.joc.2c00889 | |||||
著者版フラグ | ||||||
出版タイプ | AM | |||||
出版タイプResource | http://purl.org/coar/version/c_ab4af688f83e57aa |