ログイン
言語:

WEKO3

  • トップ
  • ランキング
To
lat lon distance
To

Field does not validate



インデックスリンク

インデックスツリー

メールアドレスを入力してください。

WEKO

One fine body…

WEKO

One fine body…

アイテム

  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
内容記述タイプ Abstract
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
出版者
出版者 ACS Publications
言語 en
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
戻る
0
views
See details
Views

Versions

Ver.1 2021-03-01 13:51:39.684435
Show All versions

Share

Mendeley Twitter Facebook Print Addthis

Cite as

エクスポート

OAI-PMH
  • OAI-PMH JPCOAR 2.0
  • OAI-PMH JPCOAR 1.0
  • OAI-PMH DublinCore
  • OAI-PMH DDI
Other Formats
  • JSON
  • BIBTEX

Confirm


Powered by WEKO3


Powered by WEKO3