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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

Hypoiodite-Catalyzed Chemoselective Tandem Oxidation of Homotryptamines to Peroxy- and Epoxytetrahydropyridoindolenines

http://hdl.handle.net/2237/0002001528
http://hdl.handle.net/2237/0002001528
ef9ae8e5-e39e-497e-903d-dc548a5cc117
名前 / ファイル ライセンス アクション
Org_Lett_2020_22_8049.pdf Org_Lett_2020_22_8049.pdf (3.2 MB)
Item type itemtype_ver1(1)
公開日 2021-10-18
タイトル
タイトル Hypoiodite-Catalyzed Chemoselective Tandem Oxidation of Homotryptamines to Peroxy- and Epoxytetrahydropyridoindolenines
言語 en
著者 Uyanik, Muhammet

× Uyanik, Muhammet

en Uyanik, Muhammet

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Tanaka, Hiroki

× Tanaka, Hiroki

en Tanaka, Hiroki

Search repository
Ishihara, Kazuaki

× Ishihara, Kazuaki

en Ishihara, Kazuaki

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 [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://pubs.acs.org/articlesonrequest/AOR-NBYYPWXXWYI8QNCM8P8K].”
内容記述
内容記述 We developed the hypoiodite-catalyzed tandem dearomative peroxycyclization of homotryptamine derivatives to peroxytetrahydropyridoindolenines under mild conditions. During the course of a mechanistic study, we found that a tandem oxidative cyclization/epoxidation as an unexpected reaction proceeded in the presence of TEMPO as an additive. Intramolecular oxidative aminocyclization of homotryptamines at the C-2 position would give tetrahydropyridoindole, a common intermediate for both reactions. Control experiments suggested that while oxidative coupling with TBHP at the C-3 position might afford peroxyindolenines, a preferential electrophilic addition of TEMPO^+, which might be generated in situ by the hypoiodite-catalyzed oxidation of TEMPO, at C-3 position followed by elimination and epoxidation might give epoxyindolenines. This serendipitous finding prompted us to develop a chemoselective divergent synthesis of peroxy- and epoxyindolenines by simple modification of the reaction conditions.
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/acs.orglett.0c03001
収録物識別子
収録物識別子タイプ PISSN
収録物識別子 1523-7060
書誌情報 en : Organic Letters

巻 22, 号 20, p. 8049-8054, 発行日 2020-10-16
ファイル公開日
日付 2021-10-18
日付タイプ Available
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