{"@context":{"@vocab":"https://cir.nii.ac.jp/schema/1.0/","rdfs":"http://www.w3.org/2000/01/rdf-schema#","dc":"http://purl.org/dc/elements/1.1/","dcterms":"http://purl.org/dc/terms/","foaf":"http://xmlns.com/foaf/0.1/","prism":"http://prismstandard.org/namespaces/basic/2.0/","cinii":"http://ci.nii.ac.jp/ns/1.0/","datacite":"https://schema.datacite.org/meta/kernel-4/","ndl":"http://ndl.go.jp/dcndl/terms/","jpcoar":"https://github.com/JPCOAR/schema/blob/master/2.0/"},"@id":"https://cir.nii.ac.jp/crid/1360567183167217536.json","@type":"Article","productIdentifier":[{"identifier":{"@type":"DOI","@value":"10.1021/ja5017206"}},{"identifier":{"@type":"URI","@value":"https://pubs.acs.org/doi/pdf/10.1021/ja5017206"}},{"identifier":{"@type":"PMID","@value":"24746095"}}],"resourceType":"学術雑誌論文(journal article)","dc:title":[{"@value":"Mechanistic Studies of Highly Enantio- and Diastereoselective Aza-Petasis–Ferrier Rearrangement Catalyzed by Chiral Phosphoric Acid"}],"description":[{"notation":[{"@value":"The precise mechanism of the highly anti- and enantioselective aza-Petasis-Ferrier (APF) rearrangement of hemiaminal vinyl ethers catalyzed by a chiral phosphoric acid was investigated by undertaking experimental and theoretical studies. The APF rearrangement is characterized by the following unique mechanistic features: (i) efficient optical kinetic resolution of the starting racemic hemiaminal vinyl ether, (ii) enantioconvergent process from racemic hemiaminal vinyl ethers to optically active β-amino aldehyde products, and (iii) anomalous temperature effects on the enantioselectivity (enantioselectivity increases as reaction temperature increases). The following experiments were conducted to elucidate the unique mechanistic features as well as to uncover the overall scheme of the present rearrangement: (A) X-ray crystallographic analysis of the recovered hemiaminal vinyl ether to determine its absolute configuration, (B) rearrangements of enantiomerically pure hemiaminal vinyl ethers to validate the stereochemical relationship between the hemiaminal vinyl ethers and β-amino aldehydes, (C) theoretical studies on the transition states of the C-O bond cleavage and C-C bond formation steps to gain an insight into the optical kinetic resolution of the hemiaminal vinyl ether and the origin of the stereoselectivity, as well as to elucidate the overall scheme of the present rearrangement, and (D) crossover experiments of two hemiaminal vinyl ethers having different vinyl ether and aliphatic substituents to comprehend the mechanism of the anomalous temperature effect and the enantioconvergent process. The results of experiments and theoretical studies fully support the proposed mechanism of the present anti- and enantioselective APF rearrangement."}]}],"creator":[{"@id":"https://cir.nii.ac.jp/crid/1420845751162563968","@type":"Researcher","personIdentifier":[{"@type":"KAKEN_RESEARCHERS","@value":"50217428"},{"@type":"NRID","@value":"1000050217428"},{"@type":"NRID","@value":"9000404635283"},{"@type":"NRID","@value":"9000001997026"},{"@type":"NRID","@value":"9000359904620"},{"@type":"NRID","@value":"9000016983044"},{"@type":"NRID","@value":"9000000842246"},{"@type":"NRID","@value":"9000002973172"},{"@type":"NRID","@value":"9000010501110"},{"@type":"NRID","@value":"9000000591557"},{"@type":"NRID","@value":"9000242696620"},{"@type":"NRID","@value":"9000314078157"},{"@type":"NRID","@value":"9000243765902"},{"@type":"NRID","@value":"9000018280393"},{"@type":"NRID","@value":"9000257707899"},{"@type":"NRID","@value":"9000017673735"},{"@type":"NRID","@value":"9000002974971"},{"@type":"NRID","@value":"9000411211076"},{"@type":"NRID","@value":"9000356639312"},{"@type":"NRID","@value":"9000010624443"},{"@type":"NRID","@value":"9000018232051"},{"@type":"NRID","@value":"9000404110042"},{"@type":"NRID","@value":"9000256027887"},{"@type":"NRID","@value":"9000021435525"},{"@type":"NRID","@value":"9000404850556"},{"@type":"NRID","@value":"9000020964490"},{"@type":"NRID","@value":"9000020997382"},{"@type":"NRID","@value":"9000399852546"},{"@type":"RESEARCHMAP","@value":"https://researchmap.jp/terada0214"}],"foaf:name":[{"@value":"Masahiro Terada"}],"jpcoar:affiliationName":[{"@value":"Department\rof Chemistry, Graduate School of Science, Tohoku University, Aoba-ku, Sendai 980-8578, Japan"},{"@value":"Research\rand Analytical Center for Giant Molecules, Graduate School of Science, Tohoku University, Aoba-ku, Sendai 980-8578, Japan"}]},{"@id":"https://cir.nii.ac.jp/crid/1380567183167217537","@type":"Researcher","foaf:name":[{"@value":"Takazumi Komuro"}],"jpcoar:affiliationName":[{"@value":"Department\rof Chemistry, Graduate School of Science, Tohoku University, Aoba-ku, Sendai 980-8578, Japan"}]},{"@id":"https://cir.nii.ac.jp/crid/1380567183167217539","@type":"Researcher","foaf:name":[{"@value":"Yasunori Toda"}],"jpcoar:affiliationName":[{"@value":"Department\rof Chemistry, Graduate School of Science, Tohoku University, Aoba-ku, Sendai 980-8578, Japan"}]},{"@id":"https://cir.nii.ac.jp/crid/1380567183167217538","@type":"Researcher","foaf:name":[{"@value":"Toshinobu Korenaga"}],"jpcoar:affiliationName":[{"@value":"Department\rof Chemistry and Bioengineering, Graduate School of Engineering, Iwate University, 4-3-5 Ueda, Morioka, Iwate-ken 020-8551, Japan"}]}],"publication":{"publicationIdentifier":[{"@type":"PISSN","@value":"00027863"},{"@type":"EISSN","@value":"15205126"}],"prism:publicationName":[{"@value":"Journal of the American Chemical Society"}],"dc:publisher":[{"@value":"American Chemical Society (ACS)"}],"prism:publicationDate":"2014-05-01","prism:volume":"136","prism:number":"19","prism:startingPage":"7044","prism:endingPage":"7057"},"reviewed":"false","url":[{"@id":"https://pubs.acs.org/doi/pdf/10.1021/ja5017206"}],"createdAt":"2014-04-18","modifiedAt":"2023-04-07","foaf:topic":[{"@id":"https://cir.nii.ac.jp/all?q=Models,%20Molecular","dc:title":"Models, Molecular"},{"@id":"https://cir.nii.ac.jp/all?q=Aldehydes","dc:title":"Aldehydes"},{"@id":"https://cir.nii.ac.jp/all?q=Kinetics","dc:title":"Kinetics"},{"@id":"https://cir.nii.ac.jp/all?q=Vinyl%20Compounds","dc:title":"Vinyl Compounds"},{"@id":"https://cir.nii.ac.jp/all?q=Phosphoric%20Acids","dc:title":"Phosphoric Acids"},{"@id":"https://cir.nii.ac.jp/all?q=Stereoisomerism","dc:title":"Stereoisomerism"},{"@id":"https://cir.nii.ac.jp/all?q=Catalysis","dc:title":"Catalysis"}],"project":[{"@id":"https://cir.nii.ac.jp/crid/1040282257117009664","@type":"Project","projectIdentifier":[{"@type":"KAKEN","@value":"23105002"},{"@type":"JGN","@value":"JP23105002"},{"@type":"URI","@value":"https://kaken.nii.ac.jp/grant/KAKENHI-PLANNED-23105002/"}],"notation":[{"@language":"ja","@value":"水素結合のネットワーク形成に基づく有機分子触媒の制御システム設計開発"},{"@language":"en","@value":"Development of Controlling System for Organocatalysts Based on the Formation of Hydrogen Bonding 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