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タイトル: | Synthesis of Polycyclic Spirocarbocycles via Acid-Promoted Ring-Contraction/Dearomative Ring-Closure Cascade of Oxapropellanes |
著者: | Ogawa, Naoki Yamaoka, Yousuke Takikawa, Hiroshi https://orcid.org/0000-0002-4414-2129 (unconfirmed) Takasu, Kiyosei https://orcid.org/0000-0002-1798-7919 (unconfirmed) |
著者名の別形: | 小川, 直希 山岡, 庸介 瀧川, 紘 高須, 清誠 |
発行日: | Sep-2019 |
出版者: | American Chemical Society (ACS) |
誌名: | Organic letters |
巻: | 21 |
号: | 18 |
開始ページ: | 7563 |
終了ページ: | 7567 |
抄録: | We report herein the development of an acid-promoted rearrangement of oxa[4.3.2]propellanes to afford polyaromatic-fused spiro[4.5]carbocycles. DFT calculations suggest that the reaction pathway involves generation of a cyclobutyl cation, ring contraction to the cyclopropylcarbinyl cation, and dearomative ring closure by an internal 2-naphthol moiety. The resulting spirocarbocycles are synthetically valuable, as they could be transformed into two different polycyclic aromatic hydrocarbons via skeletal rearrangement. Syntheses of optically pure spirocarbocycles via a central-to-axial-to-central chirality transfer are also described. |
著作権等: | 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://doi.org/10.1021/acs.orglett.9b02835. The full-text file will be made open to the public on 9 September 2020 in accordance with publisher's 'Terms and Conditions for Self-Archiving' この論文は出版社版でありません。引用の際には出版社版をご確認ご利用ください。 This is not the published version. Please cite only the published version. |
URI: | http://hdl.handle.net/2433/244810 |
DOI(出版社版): | 10.1021/acs.orglett.9b02835 |
PubMed ID: | 31497972 |
出現コレクション: | 学術雑誌掲載論文等 |
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