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タイトル: | Asymmetric systematic synthesis, structures, and (chir)optical properties of a series of dihetero[8]helicenes |
著者: | Yanagi, Tomoyuki Tanaka, Takayuki https://orcid.org/0000-0001-8018-7984 (unconfirmed) Yorimitsu, Hideki https://orcid.org/0000-0002-0153-1888 (unconfirmed) |
著者名の別形: | 柳, 智征 田中, 隆行 依光, 英樹 |
発行日: | 28-Feb-2021 |
出版者: | Royal Society of Chemistry (RSC) |
誌名: | Chemical Science |
巻: | 12 |
号: | 8 |
開始ページ: | 2784 |
終了ページ: | 2793 |
抄録: | A series of dihetero[8]helicenes have been systematically synthesized in enantiomerically enriched forms by utilizing the characteristic transformations of the organosulfur functionality. The synthetic route begins with assembling a ternaphthyl common synthetic intermediate from 2-naphthol and bissulfinylnaphthalene through an extended Pummerer reaction followed by facile multi-gram-scale resolution. The subsequent cyclization reactions into dioxa- and dithia[8]helicenes take place with excellent axial-to-helical chirality conversion. Dithia[8]helicene is further transformed into the nitrogen and the carbon analogs by replacing the two endocyclic sulfur atoms via SNAr-based skeletal reconstruction. The efficient systematic synthesis has enabled comprehensive evaluation of physical properties, which has clarified the effect of the endocyclic atoms on their structures and (chir)optical properties as well as the unexpected conformational stability of the common helical framework. |
著作権等: | © 2021 The Author(s). Published by the Royal Society of Chemistry This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. |
URI: | http://hdl.handle.net/2433/276655 |
DOI(出版社版): | 10.1039/D1SC00044F |
PubMed ID: | 34164042 |
出現コレクション: | 学術雑誌掲載論文等 |
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