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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

Emergence of Highly Enantioselective Catalytic Activity in a Helical Polymer Mediated by Deracemization of Racemic Pendants

http://hdl.handle.net/2237/0002002065
http://hdl.handle.net/2237/0002002065
e1f900b5-678f-4a77-93a0-71e5a3568f8d
名前 / ファイル ライセンス アクション
Ikai-rev.pdf Ikai-rev.pdf (6.6 MB)
Item type itemtype_ver1(1)
公開日 2022-02-10
タイトル
タイトル Emergence of Highly Enantioselective Catalytic Activity in a Helical Polymer Mediated by Deracemization of Racemic Pendants
言語 en
著者 Ikai, Tomoyuki

× Ikai, Tomoyuki

en Ikai, Tomoyuki

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Ando, Mitsuka

× Ando, Mitsuka

en Ando, Mitsuka

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Ito, Masaki

× Ito, Masaki

en Ito, Masaki

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Ishidate, Ryoma

× Ishidate, Ryoma

en Ishidate, Ryoma

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Suzuki, Nozomu

× Suzuki, Nozomu

en Suzuki, Nozomu

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Maeda, Katsuhiro

× Maeda, Katsuhiro

en Maeda, Katsuhiro

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Yashima, Eiji

× Yashima, Eiji

en 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 [https://pubs.acs.org/articlesonrequest/AOR-IPYDMMW32CQUCQHQMZBX].”
内容記述
内容記述 Any polymers composed of racemic repeating units are obviously optically inactive and hence chiral functions, such as asymmetric catalysis, will not be expected at all. Contrary to such a preconceived notion, we report an unprecedented helical polymer-based highly enantioselective organocatalyst prepared by polymerization of a racemic monomer with no catalytic activity. Both the right- and left-handed helical poly(biarylylacetylene)s (PBAs) composed of dynamically racemic 2-arylpyridyl-N-oxide monomer units with N-oxide moieties located in the vicinity of the helical polymer backbone can be produced by noncovalent interaction with a chiral alcohol through deracemization of the biaryl pendants. The macromolecular helicity and the axial chirality induced in the PBAs are retained (“memorized”) after complete removal of the chiral alcohol. Accordingly, the helical PBAs with dual static memory of the helicity and axial chirality show remarkable enantioselectivity (86% ee) for the asymmetric allylation of benzaldehyde. The enantioselectivity is slightly lower than that (96% ee) of the homochiral PBAs prepared from the corresponding enantiopure (R)- and (S)-monomers, but is comparable to that (88% ee) of the helical PBA composed of nonracemic monomers of ca. 60% ee.
言語 en
内容記述タイプ Abstract
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
関連情報
関連タイプ isVersionOf
識別子タイプ DOI
関連識別子 https://doi.org/10.1021/jacs.1c05620
収録物識別子
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 143, 号 32, p. 12725-12735, 発行日 2021-08-18
ファイル公開日
日付 2022-08-18
日付タイプ Available
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