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  1. D400 創薬科学研究科
  2. D400a 雑誌掲載論文
  3. 学術雑誌

Combined Experimental and Computational Study on Ruthenium(II)-Catalyzed Reactions of Diynes with Aldehydes and N,N‑Dimethylformamide

http://hdl.handle.net/2237/27077
http://hdl.handle.net/2237/27077
939c00bf-c5e7-4e80-8174-bd4ccc8ff89d
名前 / ファイル ライセンス アクション
JOC_MS_rev.pdf JOC_MS_rev.pdf ファイル公開日:2018/08/04 (895.1 kB)
Item type 学術雑誌論文 / Journal Article(1)
公開日 2017-11-08
タイトル
タイトル Combined Experimental and Computational Study on Ruthenium(II)-Catalyzed Reactions of Diynes with Aldehydes and N,N‑Dimethylformamide
言語 en
著者 Yoshihiko, Yamamoto

× Yoshihiko, Yamamoto

WEKO 73939

en Yoshihiko, Yamamoto

Search repository
Yuta, Okude

× Yuta, Okude

WEKO 73940

en Yuta, Okude

Search repository
Shota, Mori

× Shota, Mori

WEKO 73941

en Shota, Mori

Search repository
Masatoshi, Shibuya

× Masatoshi, Shibuya

WEKO 73942

en Masatoshi, Shibuya

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 [Journal of Organic Chemistry], copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see [ http://pubs.acs.org/articlesonrequest/AOR-gsXP3SHHURzcsmdS3cwp].”
抄録
内容記述 Cycloaddition reactions of 1,6-diynes bearing methyl terminal groups with p-anisaldehyde were conducted using a cationic ruthenium catalyst with a η^5 -pentamethylcyclopentadienyl ligand in THF at room temperature to afford dienyl ketones via ring opening of the initially formed fused pyrans. (Z)-Stereoisomers of dienyl ketones were selectively obtained using the ruthenium catalyst, whereas previously reported rhodium catalysts produced (E)-isomers. These (E)- and (Z)-selectivities are kinetically controlled as the control experiments showed that the E/Z-isomerization of (E)-dienylketone occurs at 70 °C for 10 h to afford an E/Z-ratio of almost 1:1. The origin of this characteristic stereoselectivity for the ruthenium catalyst was attributed to the direct ring opening of the CpRu^+ -coordinated pyran complex intermediates on the basis of theoretical calculations [PCM (THF) M06L/SDD-6-311++G(d,p)//B3LYP/LanL2DZ-6-31G(d)] and control experiments. The (Z)-selectivity increased when the bulkiness of the diyne terminal substituents increased. Notably, the reaction of 1,6-diynes bearing tert-butyl terminal groups with various α,β-unsaturated aldehydes exclusively afforded (Z)-dienyl ketones even at 70 °C when a cationic ruthenium complex with a smaller η^5 -cyclopentadienyl (Cp) ligand was used as the catalyst. The same Cp complex was found to be also efficient for the hydrocarbamoylative cyclization of sterically demanding 1,6-diynes bearing tertiary or quaternary carbon tethers with N,N-dimethylformamide.
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
DOI
関連タイプ isVersionOf
識別子タイプ DOI
関連識別子 https://doi.org/10.1021/acs.joc.7b01229
ISSN
収録物識別子タイプ PISSN
収録物識別子 0022-3263
書誌情報 en : Journal of Organic Chemistry

巻 82, 号 15, p. 7964-7973, 発行日 2017-08-04
著者版フラグ
値 author
URI
識別子 http://doi.org/10.1021/acs.joc.7b01229
識別子タイプ DOI
URI
識別子 http://hdl.handle.net/2237/27077
識別子タイプ HDL
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