{"_buckets": {"deposit": "0330198d-f8c7-4870-8e51-7a90dba44ba8"}, "_deposit": {"id": "24857", "owners": [], "pid": {"revision_id": 0, "type": "depid", "value": "24857"}, "status": "published"}, "_oai": {"id": "oai:nagoya.repo.nii.ac.jp:00024857", "sets": ["1905"]}, "author_link": ["73939", "73940", "73941", "73942"], "item_10_biblio_info_6": {"attribute_name": "書誌情報", "attribute_value_mlt": [{"bibliographicIssueDates": {"bibliographicIssueDate": "2017-08-04", "bibliographicIssueDateType": "Issued"}, "bibliographicIssueNumber": "15", "bibliographicPageEnd": "7973", "bibliographicPageStart": "7964", "bibliographicVolumeNumber": "82", "bibliographic_titles": [{"bibliographic_title": "Journal of Organic Chemistry", "bibliographic_titleLang": "en"}]}]}, "item_10_description_4": {"attribute_name": "抄録", "attribute_value_mlt": [{"subitem_description": "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.", "subitem_description_language": "en", "subitem_description_type": "Abstract"}]}, "item_10_identifier_60": {"attribute_name": "URI", "attribute_value_mlt": [{"subitem_identifier_type": "DOI", "subitem_identifier_uri": "http://doi.org/10.1021/acs.joc.7b01229"}, {"subitem_identifier_type": "HDL", "subitem_identifier_uri": "http://hdl.handle.net/2237/27077"}]}, "item_10_publisher_32": {"attribute_name": "出版者", "attribute_value_mlt": [{"subitem_publisher": "ACS Publications", "subitem_publisher_language": "en"}]}, "item_10_relation_11": {"attribute_name": "DOI", "attribute_value_mlt": [{"subitem_relation_type": "isVersionOf", "subitem_relation_type_id": {"subitem_relation_type_id_text": "https://doi.org/10.1021/acs.joc.7b01229", "subitem_relation_type_select": "DOI"}}]}, "item_10_rights_12": {"attribute_name": "権利", "attribute_value_mlt": [{"subitem_rights": "“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].”", "subitem_rights_language": "en"}]}, "item_10_select_15": {"attribute_name": "著者版フラグ", "attribute_value_mlt": [{"subitem_select_item": "author"}]}, "item_10_source_id_7": {"attribute_name": "ISSN", "attribute_value_mlt": [{"subitem_source_identifier": "0022-3263", "subitem_source_identifier_type": "PISSN"}]}, "item_1615787544753": {"attribute_name": "出版タイプ", "attribute_value_mlt": [{"subitem_version_resource": "http://purl.org/coar/version/c_ab4af688f83e57aa", "subitem_version_type": "AM"}]}, "item_access_right": {"attribute_name": "アクセス権", "attribute_value_mlt": [{"subitem_access_right": "open access", "subitem_access_right_uri": "http://purl.org/coar/access_right/c_abf2"}]}, "item_creator": {"attribute_name": "著者", "attribute_type": "creator", "attribute_value_mlt": [{"creatorNames": [{"creatorName": "Yoshihiko, Yamamoto", "creatorNameLang": "en"}], "nameIdentifiers": [{"nameIdentifier": "73939", "nameIdentifierScheme": "WEKO"}]}, {"creatorNames": [{"creatorName": "Yuta, Okude", "creatorNameLang": "en"}], "nameIdentifiers": [{"nameIdentifier": "73940", "nameIdentifierScheme": "WEKO"}]}, {"creatorNames": [{"creatorName": "Shota, Mori", "creatorNameLang": "en"}], "nameIdentifiers": [{"nameIdentifier": "73941", "nameIdentifierScheme": "WEKO"}]}, {"creatorNames": [{"creatorName": "Masatoshi, Shibuya", "creatorNameLang": "en"}], "nameIdentifiers": [{"nameIdentifier": "73942", "nameIdentifierScheme": "WEKO"}]}]}, "item_files": {"attribute_name": "ファイル情報", "attribute_type": "file", "attribute_value_mlt": [{"accessrole": "open_date", "date": [{"dateType": "Available", "dateValue": "2018-08-04"}], "displaytype": "detail", "download_preview_message": "", "file_order": 0, "filename": "JOC_MS_rev.pdf", "filesize": [{"value": "895.1 kB"}], "format": "application/pdf", "future_date_message": "", "is_thumbnail": false, "licensetype": "license_note", "mimetype": "application/pdf", "size": 895100.0, "url": {"label": "JOC_MS_rev.pdf ファイル公開日:2018/08/04", "objectType": "fulltext", "url": "https://nagoya.repo.nii.ac.jp/record/24857/files/JOC_MS_rev.pdf"}, "version_id": "39f7154e-2d01-4970-a6a4-754faf28df69"}]}, "item_language": {"attribute_name": "言語", "attribute_value_mlt": [{"subitem_language": "eng"}]}, "item_resource_type": {"attribute_name": "資源タイプ", "attribute_value_mlt": [{"resourcetype": "journal article", "resourceuri": "http://purl.org/coar/resource_type/c_6501"}]}, "item_title": "Combined Experimental and Computational Study on Ruthenium(II)-Catalyzed Reactions of Diynes with Aldehydes and N,N‑Dimethylformamide", "item_titles": {"attribute_name": "タイトル", "attribute_value_mlt": [{"subitem_title": "Combined Experimental and Computational Study on Ruthenium(II)-Catalyzed Reactions of Diynes with Aldehydes and N,N‑Dimethylformamide", "subitem_title_language": "en"}]}, "item_type_id": "10", "owner": "1", "path": ["1905"], "permalink_uri": "http://hdl.handle.net/2237/27077", "pubdate": {"attribute_name": "PubDate", "attribute_value": "2017-11-08"}, "publish_date": "2017-11-08", "publish_status": "0", "recid": "24857", "relation": {}, "relation_version_is_last": true, "title": ["Combined Experimental and Computational Study on Ruthenium(II)-Catalyzed Reactions of Diynes with Aldehydes and N,N‑Dimethylformamide"], "weko_shared_id": -1}