{"created":"2021-03-01T06:15:25.615272+00:00","id":12514,"links":{},"metadata":{"_buckets":{"deposit":"71a7ef96-c2c5-47b4-82e7-e8e27750f33b"},"_deposit":{"id":"12514","owners":[],"pid":{"revision_id":0,"type":"depid","value":"12514"},"status":"published"},"_oai":{"id":"oai:soar-ir.repo.nii.ac.jp:00012514","sets":["1221:1222"]},"author_link":["38208","38209","38210","38211","38212","38213","38214","38215","38216","38217"],"item_1628147817048":{"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_6_biblio_info_6":{"attribute_name":"書誌情報","attribute_value_mlt":[{"bibliographicIssueDates":{"bibliographicIssueDate":"2010-04-17","bibliographicIssueDateType":"Issued"},"bibliographicIssueNumber":"16","bibliographicPageEnd":"3089","bibliographicPageStart":"3070","bibliographicVolumeNumber":"66","bibliographic_titles":[{"bibliographic_title":"Tetrahedron"}]}]},"item_6_description_20":{"attribute_name":"抄録","attribute_value_mlt":[{"subitem_description":"High enantioselectivities (94–96% ee) were obtained for the inverse electron-demand 1,3-dipolar cycloadditions between cyclohexyl vinyl ether and 2-benzopyrylium-4-olate generated via Rh₂(OAc)₄-catalyzed decomposition of o-methoxycarbonyl-α-diazoacetophenone. The reactions were effectively catalyzed by Eu(OTf)₃, Ho(OTf)₃, or Gd(OTf)₃ complexes (10 mol %) of chiral 2,6-bis[(4S,5S)-4,5-diphenyl-2-oxazolinyl]pyridine. The reactions with the other electron-rich dipolarophiles such as allyl alcohol, 2,3-dihydrofuran, and butyl-tert-butyldimethylsilylketene acetal showed moderate enanantioselectivities (60–73% ee). Good to high enantioselectivities (73–97% ee) were also obtained for the cycloadditions between 3-acyl-2-benzopyrylium-4-olates, generated from methyl 2-(2-diazo-1,3-dioxoalkyl)benzoates and butyl or cyclohexyl vinyl ethers, in the presence of binaphthyldiimine (BINIM)–Ni(II) complexes (10 mol %). Under similar conditions, the reaction between methyl 2-(2-diazo-1,3-dioxohexyl)benzoate and 2,3-dihydrofuran was highly endo-selective, and moderately enantioselective (70% ee). For the BINIM–Ni(II)-catalyzed reactions of cyclohexyl vinyl ether, the use of an epoxyindanone as the 3-acyl-2-benzopyrylium-4-olate precursor revealed that the chiral Lewis acid can function as a catalyst for asymmetric induction. The scope of the cyclic carbonyl ylides was extended to those generated from 1-diazo-2,5-pentanedione derivatives, which were reacted with butyl or TBS vinyl ether and catalyzed using the (4S,5S)-Pybox-4,5-Ph₂–Lu(OTf)₃ complex to give good levels of asymmetric inductions (75–84% ee).","subitem_description_type":"Abstract"}]},"item_6_description_30":{"attribute_name":"資源タイプ（コンテンツの種類）","attribute_value_mlt":[{"subitem_description":"Article","subitem_description_type":"Other"}]},"item_6_description_5":{"attribute_name":"引用","attribute_value_mlt":[{"subitem_description":"Tetrahedron. 66(16):3070-3089 (2010)","subitem_description_type":"Other"}]},"item_6_link_3":{"attribute_name":"信州大学研究者総覧へのリンク","attribute_value_mlt":[{"subitem_link_text":"Suga, Hiroyuki","subitem_link_url":"http://soar-rd.shinshu-u.ac.jp/profile/ja.HmShyVfp.html"}]},"item_6_link_67":{"attribute_name":"WoS","attribute_value_mlt":[{"subitem_link_url":"http://gateway.isiknowledge.com/gateway/Gateway.cgi?&GWVersion=2&SrcAuth=ShinshuUniv&SrcApp=ShinshuUniv&DestLinkType=FullRecord&DestApp=WOS&KeyUT=000276588400022"}]},"item_6_publisher_4":{"attribute_name":"出版者","attribute_value_mlt":[{"subitem_publisher":"PERGAMON-ELSEVIER SCIENCE LTD"}]},"item_6_relation_48":{"attribute_name":"DOI","attribute_value_mlt":[{"subitem_relation_name":[{"subitem_relation_name_text":"10.1016/j.tet.2010.01.095"}],"subitem_relation_type_id":{"subitem_relation_type_id_text":"https://doi.org/10.1016/j.tet.2010.01.095","subitem_relation_type_select":"DOI"}}]},"item_6_rights_62":{"attribute_name":"権利","attribute_value_mlt":[{"subitem_rights":"Copyright (c) 2010 Elsevier Ltd."}]},"item_6_source_id_35":{"attribute_name":"ISSN","attribute_value_mlt":[{"subitem_source_identifier":"0040-4020","subitem_source_identifier_type":"ISSN"}]},"item_6_source_id_40":{"attribute_name":"書誌レコードID","attribute_value_mlt":[{"subitem_source_identifier":"AA11539786","subitem_source_identifier_type":"NCID"}]},"item_creator":{"attribute_name":"著者","attribute_type":"creator","attribute_value_mlt":[{"creatorNames":[{"creatorName":"Suga,  Hiroyuki"}],"nameIdentifiers":[{}]},{"creatorNames":[{"creatorName":"Higuchi,  Satoshi"}],"nameIdentifiers":[{}]},{"creatorNames":[{"creatorName":"Ohtsuka,  Motoo"}],"nameIdentifiers":[{}]},{"creatorNames":[{"creatorName":"Ishimoto,  Daisuke"}],"nameIdentifiers":[{}]},{"creatorNames":[{"creatorName":"Arikawa,  Tadashi"}],"nameIdentifiers":[{}]},{"creatorNames":[{"creatorName":"Hashimoto,  Yuta"}],"nameIdentifiers":[{}]},{"creatorNames":[{"creatorName":"Misawa,  Shunta"}],"nameIdentifiers":[{}]},{"creatorNames":[{"creatorName":"Tsuchida,  Teruko"}],"nameIdentifiers":[{}]},{"creatorNames":[{"creatorName":"Kakehi,  Akikazu"}],"nameIdentifiers":[{}]},{"creatorNames":[{"creatorName":"Baba,  Toshihide"}],"nameIdentifiers":[{}]}]},"item_files":{"attribute_name":"ファイル情報","attribute_type":"file","attribute_value_mlt":[{"accessrole":"open_date","date":[{"dateType":"Available","dateValue":"2015-09-28"}],"displaytype":"detail","filename":"Inverse_Electron_Demand_Asymmetric_Cycloadditions.pdf","filesize":[{"value":"1.4 MB"}],"format":"application/pdf","licensetype":"license_note","mimetype":"application/pdf","url":{"label":"Inverse_Electron_Demand_Asymmetric_Cycloadditions.pdf","url":"https://soar-ir.repo.nii.ac.jp/record/12514/files/Inverse_Electron_Demand_Asymmetric_Cycloadditions.pdf"},"version_id":"329e58bc-d428-476b-9a54-98b7ff1ac7b4"}]},"item_keyword":{"attribute_name":"キーワード","attribute_value_mlt":[{"subitem_subject":"1,3-Dipolar cycloaddition","subitem_subject_scheme":"Other"},{"subitem_subject":"Carbonyl ylide","subitem_subject_scheme":"Other"},{"subitem_subject":"Chiral Lewis acid","subitem_subject_scheme":"Other"},{"subitem_subject":"Asymmetric synthesis","subitem_subject_scheme":"Other"},{"subitem_subject":"Metal catalyst","subitem_subject_scheme":"Other"},{"subitem_subject":"Diazocarbonyl compound","subitem_subject_scheme":"Other"}]},"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":"Inverse electron demand asymmetric cycloadditions of cyclic carbonyl ylides catalyzed by chiral Lewis acids-Scope and limitations of diazo and olefinic substrates","item_titles":{"attribute_name":"タイトル","attribute_value_mlt":[{"subitem_title":"Inverse electron demand asymmetric cycloadditions of cyclic carbonyl ylides catalyzed by chiral Lewis acids-Scope and limitations of diazo and olefinic substrates","subitem_title_language":"en"}]},"item_type_id":"6","owner":"1","path":["1222"],"pubdate":{"attribute_name":"PubDate","attribute_value":"2010-10-26"},"publish_date":"2010-10-26","publish_status":"0","recid":"12514","relation_version_is_last":true,"title":["Inverse electron demand asymmetric cycloadditions of cyclic carbonyl ylides catalyzed by chiral Lewis acids-Scope and limitations of diazo and olefinic substrates"],"weko_creator_id":"1","weko_shared_id":-1},"updated":"2022-12-14T04:30:14.345240+00:00"}