{"@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/1363670318406491648.json","@type":"Article","productIdentifier":[{"identifier":{"@type":"DOI","@value":"10.1002/ejoc.200300387"}},{"identifier":{"@type":"URI","@value":"https://api.wiley.com/onlinelibrary/tdm/v1/articles/10.1002%2Fejoc.200300387"}},{"identifier":{"@type":"URI","@value":"https://chemistry-europe.onlinelibrary.wiley.com/doi/pdf/10.1002/ejoc.200300387"}}],"dc:title":[{"@value":"Efficient Solution‐Phase Parallel Synthesis of 4‐Substituted <i>N</i>‐Protected Piperidines"}],"description":[{"type":"abstract","notation":[{"@value":"<jats:title>Abstract</jats:title><jats:p>Practical conditions for the synthesis of 4‐substituted <jats:italic>N</jats:italic>‐protected piperidines through CuCN·2LiBr‐catalyzed organozinc additions to 1‐acylpyridinium salts and subsequent hydrogen‐transfer hydrogenation have been established. The reaction sequence is performed at room temperature and provides 4‐substituted <jats:italic>N</jats:italic>‐protected piperidines in excellent overall yields without the isolation of intermediate dihydropyridines. In those cases in which the organozinc addition results in mixtures of 2‐ and 4‐substituted dihydropyridines, the 2‐substituted isomers are efficiently scavenged with maleic anhydride and subsequently removed by a mild extractive workup with NaHCO<jats:sub>3</jats:sub> (sat.). The <jats:italic>N</jats:italic>‐acyl group can conveniently be exchanged from <jats:italic>N</jats:italic>‐phenoxycarbonyl to <jats:italic>N</jats:italic>‐<jats:italic>t</jats:italic>Boc, thus allowing orthogonal deprotection strategies. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)</jats:p>"}]}],"creator":[{"@id":"https://cir.nii.ac.jp/crid/1383670318406491649","@type":"Researcher","foaf:name":[{"@value":"Xiaoyang Wang"}]},{"@id":"https://cir.nii.ac.jp/crid/1383670318406491650","@type":"Researcher","foaf:name":[{"@value":"Anna M. Kauppi"}]},{"@id":"https://cir.nii.ac.jp/crid/1383670318406491648","@type":"Researcher","foaf:name":[{"@value":"Roger Olsson"}]},{"@id":"https://cir.nii.ac.jp/crid/1383670318406491651","@type":"Researcher","foaf:name":[{"@value":"Fredrik Almqvist"}]}],"publication":{"publicationIdentifier":[{"@type":"PISSN","@value":"1434193X"},{"@type":"EISSN","@value":"10990690"}],"prism:publicationName":[{"@value":"European Journal of Organic Chemistry"}],"dc:publisher":[{"@value":"Wiley"}],"prism:publicationDate":"2003-11-19","prism:volume":"2003","prism:number":"23","prism:startingPage":"4586","prism:endingPage":"4592"},"reviewed":"false","dc:rights":["http://onlinelibrary.wiley.com/termsAndConditions#vor"],"url":[{"@id":"https://api.wiley.com/onlinelibrary/tdm/v1/articles/10.1002%2Fejoc.200300387"},{"@id":"https://chemistry-europe.onlinelibrary.wiley.com/doi/pdf/10.1002/ejoc.200300387"}],"createdAt":"2003-11-20","modifiedAt":"2025-10-13","relatedProduct":[{"@id":"https://cir.nii.ac.jp/crid/1360004230101837696","@type":"Article","resourceType":"学術雑誌論文(journal article)","relationType":["isReferencedBy"],"jpcoar:relatedTitle":[{"@value":"Reissert‐Type Acylation with Acylzirconocene Chloride Complexes"}]},{"@id":"https://cir.nii.ac.jp/crid/1360306905180439040","@type":"Article","resourceType":"学術雑誌論文(journal article)","relationType":["isReferencedBy"],"jpcoar:relatedTitle":[{"@value":"Unimolecular Fragment Coupling and Single Carbon Atom Doping as Tools for Structural Reprogramming"}]},{"@id":"https://cir.nii.ac.jp/crid/1360568468046634368","@type":"Article","resourceType":"学術雑誌論文(journal article)","relationType":["isReferencedBy"],"jpcoar:relatedTitle":[{"@value":"Nickel-Catalyzed Decarboxylation of Aryl Carbamates for Converting Phenols into Aromatic Amines"}]}],"dataSourceIdentifier":[{"@type":"CROSSREF","@value":"10.1002/ejoc.200300387"},{"@type":"CROSSREF","@value":"10.1002/ejoc.201301264_references_DOI_2TX76zwWSlJaAZSRME4Xv0Ev5mt"},{"@type":"CROSSREF","@value":"10.1021/acs.accounts.5c00050_references_DOI_2TX76zwWSlJaAZSRME4Xv0Ev5mt"},{"@type":"CROSSREF","@value":"10.1021/jacs.9b02751_references_DOI_2TX76zwWSlJaAZSRME4Xv0Ev5mt"}]}