{"@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/1362825893972370304.json","@type":"Article","productIdentifier":[{"identifier":{"@type":"DOI","@value":"10.1002/chem.201905773"}},{"identifier":{"@type":"URI","@value":"https://api.wiley.com/onlinelibrary/tdm/v1/articles/10.1002%2Fchem.201905773"}},{"identifier":{"@type":"URI","@value":"https://onlinelibrary.wiley.com/doi/pdf/10.1002/chem.201905773"}},{"identifier":{"@type":"URI","@value":"https://onlinelibrary.wiley.com/doi/full-xml/10.1002/chem.201905773"}},{"identifier":{"@type":"URI","@value":"https://chemistry-europe.onlinelibrary.wiley.com/doi/pdf/10.1002/chem.201905773"}}],"dc:title":[{"@value":"Functionalization of Piperidine Derivatives for the Site‐Selective and Stereoselective Synthesis of Positional Analogues of Methylphenidate"}],"description":[{"type":"abstract","notation":[{"@value":"<jats:title>Abstract</jats:title><jats:p>Rhodium‐catalyzed C−H insertions and cyclopropanations of donor/acceptor carbenes have been used for the synthesis of positional analogues of methylphenidate. The site selectivity is controlled by the catalyst and the amine protecting group. C−H functionalization of <jats:italic>N</jats:italic>‐Boc‐piperidine using Rh<jats:sub>2</jats:sub>(<jats:italic>R</jats:italic>‐TCPTAD)<jats:sub>4</jats:sub>, or <jats:italic>N</jats:italic>‐brosyl‐piperidine using Rh<jats:sub>2</jats:sub>(<jats:italic>R</jats:italic>‐TPPTTL)<jats:sub>4</jats:sub> generated 2‐substitited analogues. In contrast, when <jats:italic>N</jats:italic>‐α‐oxoarylacetyl‐piperidines were used in combination with Rh<jats:sub>2</jats:sub>(<jats:italic>S</jats:italic>‐2‐Cl‐5‐BrTPCP)<jats:sub>4</jats:sub>, the C−H functionalization produced 4‐susbstiuted analogues. Finally, the 3‐substituted analogues were prepared indirectly by cyclopropanation of <jats:italic>N</jats:italic>‐Boc‐tetrahydropyridine followed by reductive regio‐ and stereoselective ring‐opening of the cyclopropanes.</jats:p>"}]}],"creator":[{"@id":"https://cir.nii.ac.jp/crid/1382825893972370306","@type":"Researcher","foaf:name":[{"@value":"Wenbin Liu"}],"jpcoar:affiliationName":[{"@value":"Department of Chemistry Emory University  1515 Dickey Drive Atlanta GA 30322 USA"}]},{"@id":"https://cir.nii.ac.jp/crid/1382825893972370305","@type":"Researcher","foaf:name":[{"@value":"Tobias Babl"}],"jpcoar:affiliationName":[{"@value":"Department of Chemistry Emory University  1515 Dickey Drive Atlanta GA 30322 USA"},{"@value":"Institute of Organic Chemistry, University of Regensburg  Universitätsstrasse 31 93053 Regensburg Germany"}]},{"@id":"https://cir.nii.ac.jp/crid/1382825893972370308","@type":"Researcher","foaf:name":[{"@value":"Alexander Röther"}],"jpcoar:affiliationName":[{"@value":"Institute of Organic Chemistry, University of Regensburg  Universitätsstrasse 31 93053 Regensburg Germany"}]},{"@id":"https://cir.nii.ac.jp/crid/1382825893972370307","@type":"Researcher","foaf:name":[{"@value":"Oliver Reiser"}],"jpcoar:affiliationName":[{"@value":"Institute of Organic Chemistry, University of Regensburg  Universitätsstrasse 31 93053 Regensburg Germany"}]},{"@id":"https://cir.nii.ac.jp/crid/1382825893972370304","@type":"Researcher","foaf:name":[{"@value":"Huw M. L. Davies"}],"jpcoar:affiliationName":[{"@value":"Department of Chemistry Emory University  1515 Dickey Drive Atlanta GA 30322 USA"}]}],"publication":{"publicationIdentifier":[{"@type":"PISSN","@value":"09476539"},{"@type":"EISSN","@value":"15213765"}],"prism:publicationName":[{"@value":"Chemistry – A European Journal"}],"dc:publisher":[{"@value":"Wiley"}],"prism:publicationDate":"2020-03-09","prism:volume":"26","prism:number":"19","prism:startingPage":"4236","prism:endingPage":"4241"},"reviewed":"false","dc:rights":["http://creativecommons.org/licenses/by-nc-nd/4.0/"],"url":[{"@id":"https://api.wiley.com/onlinelibrary/tdm/v1/articles/10.1002%2Fchem.201905773"},{"@id":"https://onlinelibrary.wiley.com/doi/pdf/10.1002/chem.201905773"},{"@id":"https://onlinelibrary.wiley.com/doi/full-xml/10.1002/chem.201905773"},{"@id":"https://chemistry-europe.onlinelibrary.wiley.com/doi/pdf/10.1002/chem.201905773"}],"createdAt":"2019-12-24","modifiedAt":"2025-10-12","relatedProduct":[{"@id":"https://cir.nii.ac.jp/crid/1360013168732750976","@type":"Article","resourceType":"学術雑誌論文(journal article)","relationType":["isReferencedBy"],"jpcoar:relatedTitle":[{"@value":"Non-Directed β- or γ-C(sp3)–H Functionalization of Saturated Nitrogen-Containing Heterocycles"}]},{"@id":"https://cir.nii.ac.jp/crid/1390571481510240640","@type":"Article","relationType":["isReferencedBy"],"jpcoar:relatedTitle":[{"@language":"en","@value":"Enantioselective Cooperative Catalysis within Frustrated Lewis Pair Complexes"}]},{"@id":"https://cir.nii.ac.jp/crid/2051151842062065792","@type":"Article","resourceType":"学術雑誌論文(journal article)","relationType":["isReferencedBy"],"jpcoar:relatedTitle":[{"@value":"Total synthesis of lyconesidine B : approach to a three-dimensional tetracyclic skeleton of amine-type fawcettimine core and studies of asymmetric synthesis"}]}],"dataSourceIdentifier":[{"@type":"CROSSREF","@value":"10.1002/chem.201905773"},{"@type":"CROSSREF","@value":"10.1055/a-1483-4575_references_DOI_QQaAk4HfRs52dHvwzNEUGAWFFLb"},{"@type":"CROSSREF","@value":"10.1246/bcsj.20220049_references_DOI_QQaAk4HfRs52dHvwzNEUGAWFFLb"},{"@type":"CROSSREF","@value":"10.5059/yukigoseikyokaishi.79.1065_references_DOI_QQaAk4HfRs52dHvwzNEUGAWFFLb"}]}