{"@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/1361137044311522304.json","@type":"Article","productIdentifier":[{"identifier":{"@type":"DOI","@value":"10.1002/anie.201808509"}},{"identifier":{"@type":"URI","@value":"https://api.wiley.com/onlinelibrary/tdm/v1/articles/10.1002%2Fanie.201808509"}},{"identifier":{"@type":"URI","@value":"https://onlinelibrary.wiley.com/doi/pdf/10.1002/anie.201808509"}},{"identifier":{"@type":"URI","@value":"https://onlinelibrary.wiley.com/doi/full-xml/10.1002/anie.201808509"}}],"dc:title":[{"@value":"Rhodium‐Catalyzed Enantioselective Defluorinative α‐Arylation of Secondary Amides"}],"description":[{"type":"abstract","notation":[{"@value":"<jats:title>Abstract</jats:title><jats:p>We exploited the reactivity of an electronically biased Michael acceptor to perform a defluorinative α‐arylation reaction using a chiral diene(L*)‐rhodium catalyst. Through this methodology, we are able to obtain various secondary amides, containing a tertiary α‐stereocenter and a β,γ‐unsaturated <jats:italic>gem</jats:italic>‐difluoro olefin, with excellent enantioselectivities. This methodology addresses the limitations of the previously described α‐arylation methods to construct stereo‐labile tertiary α‐stereocenters. Further investigation of the reaction via in situ <jats:sup>19</jats:sup>F NMR monitoring suggests that the formation of the product leads to the inhibition of the active rhodium catalyst.</jats:p>"}]}],"creator":[{"@id":"https://cir.nii.ac.jp/crid/1381137044311522304","@type":"Researcher","foaf:name":[{"@value":"Young Jin Jang"}],"jpcoar:affiliationName":[{"@value":"Davenport Research Laboratories Department of Chemistry University of Toronto  Toronto Ontario M5S 3H6 Canada"}]},{"@id":"https://cir.nii.ac.jp/crid/1381137044311522305","@type":"Researcher","foaf:name":[{"@value":"Daniel Rose"}],"jpcoar:affiliationName":[{"@value":"Davenport Research Laboratories Department of Chemistry University of Toronto  Toronto Ontario M5S 3H6 Canada"}]},{"@id":"https://cir.nii.ac.jp/crid/1381137044311522307","@type":"Researcher","foaf:name":[{"@value":"Bijan Mirabi"}],"jpcoar:affiliationName":[{"@value":"Davenport Research Laboratories Department of Chemistry University of Toronto  Toronto Ontario M5S 3H6 Canada"}]},{"@id":"https://cir.nii.ac.jp/crid/1381137044311522306","@type":"Researcher","foaf:name":[{"@value":"Mark Lautens"}],"jpcoar:affiliationName":[{"@value":"Davenport Research Laboratories Department of Chemistry University of Toronto  Toronto Ontario M5S 3H6 Canada"}]}],"publication":{"publicationIdentifier":[{"@type":"PISSN","@value":"14337851"},{"@type":"EISSN","@value":"15213773"}],"prism:publicationName":[{"@value":"Angewandte Chemie International Edition"}],"dc:publisher":[{"@value":"Wiley"}],"prism:publicationDate":"2018-11-08","prism:volume":"57","prism:number":"49","prism:startingPage":"16147","prism:endingPage":"16151"},"reviewed":"false","dc:rights":["http://onlinelibrary.wiley.com/termsAndConditions#vor"],"url":[{"@id":"https://api.wiley.com/onlinelibrary/tdm/v1/articles/10.1002%2Fanie.201808509"},{"@id":"https://onlinelibrary.wiley.com/doi/pdf/10.1002/anie.201808509"},{"@id":"https://onlinelibrary.wiley.com/doi/full-xml/10.1002/anie.201808509"}],"createdAt":"2018-10-10","modifiedAt":"2023-09-15","relatedProduct":[{"@id":"https://cir.nii.ac.jp/crid/1050022476722772736","@type":"Article","resourceType":"学術雑誌論文(journal article)","relationType":["isReferencedBy"],"jpcoar:relatedTitle":[{"@language":"en","@value":"Rhodium(III)-Catalyzed β-Arylation and -Alkenylation of α-Trifluoromethylacrylic Acid"}]},{"@id":"https://cir.nii.ac.jp/crid/1360568467274973184","@type":"Article","resourceType":"学術雑誌論文(journal article)","relationType":["isReferencedBy"],"jpcoar:relatedTitle":[{"@value":"Recent advances of achiral and chiral diene ligands in transition-metal catalyses"}]},{"@id":"https://cir.nii.ac.jp/crid/1360576118734845568","@type":"Article","resourceType":"学術雑誌論文(journal article)","relationType":["isReferencedBy"],"jpcoar:relatedTitle":[{"@value":"Nickel‐Catalyzed Reductive Allyl−Aryl Cross‐Electrophile Coupling via Allylic C−F Bond Activation"}]},{"@id":"https://cir.nii.ac.jp/crid/1360861704788365440","@type":"Article","resourceType":"学術雑誌論文(journal article)","relationType":["isReferencedBy"],"jpcoar:relatedTitle":[{"@value":"Cu(I)‐Catalyzed Enantioselective γ‐Boryl Substitution of Trifluoromethyl‐ and Silyl‐Substituted Alkenes"}]},{"@id":"https://cir.nii.ac.jp/crid/2051996266988242944","@type":"Article","relationType":["isReferencedBy"],"jpcoar:relatedTitle":[{"@value":"Catalytic enantioselective allylic C-F bond functionalization"}]}],"dataSourceIdentifier":[{"@type":"CROSSREF","@value":"10.1002/anie.201808509"},{"@type":"CROSSREF","@value":"10.1246/cl.190024_references_DOI_a4HYbQPoA6PWJRIkIw5cELHDlIb"},{"@type":"CROSSREF","@value":"10.1016/j.tetlet.2019.07.015_references_DOI_a4HYbQPoA6PWJRIkIw5cELHDlIb"},{"@type":"CROSSREF","@value":"10.1246/cl.200826_references_DOI_a4HYbQPoA6PWJRIkIw5cELHDlIb"},{"@type":"CROSSREF","@value":"10.1002/chem.202103643_references_DOI_a4HYbQPoA6PWJRIkIw5cELHDlIb"},{"@type":"CROSSREF","@value":"10.1002/ejoc.202200664_references_DOI_a4HYbQPoA6PWJRIkIw5cELHDlIb"}]}