{"_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"}, "item_10_biblio_info_6": {"attribute_name": "\u66f8\u8a8c\u60c5\u5831", "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"}]}]}, "item_10_description_4": {"attribute_name": "\u6284\u9332", "attribute_value_mlt": [{"subitem_description": "Cycloaddition reactions of 1,6-diynes bearing\nmethyl terminal groups with p-anisaldehyde were conducted\nusing a cationic ruthenium catalyst with a \u03b7^5\n-pentamethylcyclopentadienyl\nligand in THF at room temperature to afford\ndienyl ketones via ring opening of the initially formed fused\npyrans. (Z)-Stereoisomers of dienyl ketones were selectively\nobtained using the ruthenium catalyst, whereas previously reported rhodium catalysts produced (E)-isomers. These (E)- and\n(Z)-selectivities are kinetically controlled as the control experiments showed that the E/Z-isomerization of (E)-dienylketone\noccurs at 70 \u00b0C for 10 h to afford an E/Z-ratio of almost 1:1. The origin of this characteristic stereoselectivity for the ruthenium\ncatalyst was attributed to the direct ring opening of the CpRu^+\n-coordinated pyran complex intermediates on the basis of\ntheoretical calculations [PCM (THF) M06L/SDD-6-311++G(d,p)//B3LYP/LanL2DZ-6-31G(d)] and control experiments.\nThe (Z)-selectivity increased when the bulkiness of the diyne terminal substituents increased. Notably, the reaction of 1,6-diynes\nbearing tert-butyl terminal groups with various \u03b1,\u03b2-unsaturated aldehydes exclusively afforded (Z)-dienyl ketones even at 70 \u00b0C\nwhen a cationic ruthenium complex with a smaller \u03b7^5\n-cyclopentadienyl (Cp) ligand was used as the catalyst. The same Cp\ncomplex was found to be also efficient for the hydrocarbamoylative cyclization of sterically demanding 1,6-diynes bearing tertiary\nor quaternary carbon tethers with N,N-dimethylformamide.", "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": "\u51fa\u7248\u8005", "attribute_value_mlt": [{"subitem_publisher": "ACS Publications"}]}, "item_10_rights_12": {"attribute_name": "\u6a29\u5229", "attribute_value_mlt": [{"subitem_rights": "\u201cThis document is the Accepted Manuscript version of a Published Work that appeared in final form in [Journal of Organic Chemistry], copyright \u00a9 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].\u201d"}]}, "item_10_select_15": {"attribute_name": "\u8457\u8005\u7248\u30d5\u30e9\u30b0", "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": "ISSN"}]}, "item_creator": {"attribute_name": "\u8457\u8005", "attribute_type": "creator", "attribute_value_mlt": [{"creatorNames": [{"creatorName": "Yoshihiko, Yamamoto"}], "nameIdentifiers": [{"nameIdentifier": "73939", "nameIdentifierScheme": "WEKO"}]}, {"creatorNames": [{"creatorName": "Yuta, Okude"}], "nameIdentifiers": [{"nameIdentifier": "73940", "nameIdentifierScheme": "WEKO"}]}, {"creatorNames": [{"creatorName": "Shota, Mori"}], "nameIdentifiers": [{"nameIdentifier": "73941", "nameIdentifierScheme": "WEKO"}]}, {"creatorNames": [{"creatorName": "Masatoshi, Shibuya"}], "nameIdentifiers": [{"nameIdentifier": "73942", "nameIdentifierScheme": "WEKO"}]}]}, "item_files": {"attribute_name": "\u30d5\u30a1\u30a4\u30eb\u60c5\u5831", "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_free", "mimetype": "application/pdf", "size": 895100.0, "url": {"label": "JOC_MS_rev.pdf \u30d5\u30a1\u30a4\u30eb\u516c\u958b\u65e5:2018/08/04", "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": "\u8a00\u8a9e", "attribute_value_mlt": [{"subitem_language": "eng"}]}, "item_resource_type": {"attribute_name": "\u8cc7\u6e90\u30bf\u30a4\u30d7", "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\u2011Dimethylformamide", "item_titles": {"attribute_name": "\u30bf\u30a4\u30c8\u30eb", "attribute_value_mlt": [{"subitem_title": "Combined Experimental and Computational Study on Ruthenium(II)-Catalyzed Reactions of Diynes with Aldehydes and N,N\u2011Dimethylformamide"}]}, "item_type_id": "10", "owner": "1", "path": ["1903/1904/1905"], "permalink_uri": "http://hdl.handle.net/2237/27077", "pubdate": {"attribute_name": "\u516c\u958b\u65e5", "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\u2011Dimethylformamide"], "weko_shared_id": null}