{"@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/1362262946352273792.json","@type":"Article","productIdentifier":[{"identifier":{"@type":"DOI","@value":"10.1002/chem.200903537"}},{"identifier":{"@type":"URI","@value":"https://api.wiley.com/onlinelibrary/tdm/v1/articles/10.1002%2Fchem.200903537"}},{"identifier":{"@type":"URI","@value":"https://chemistry-europe.onlinelibrary.wiley.com/doi/pdf/10.1002/chem.200903537"}}],"dc:title":[{"@value":"A 4‐Hydroxypyrrolidine‐Catalyzed Mannich Reaction of Aldehydes: Control of <i>anti‐</i>Selectivity by Hydrogen Bonding Assisted by Brønsted Acids"}],"description":[{"type":"abstract","notation":[{"@value":"<jats:title>Abstract</jats:title><jats:p>An <jats:italic>anti</jats:italic>‐selective Mannich reaction of aldehydes with <jats:italic>N</jats:italic>‐sulfonyl imines has been developed by using a 4‐hydroxypyrrolidine in combination with an external Brønsted acid. The catalyst design is based on three elements: the α‐substituent of the pyrrolidine, the 4‐hydroxy group, and the Brønsted acid, the combination of which is essential for high chemical and stereochemical efficiency. The reaction works with aromatic aldehyde‐derived imines, which have rarely been employed in previously reported enamine‐based <jats:italic>anti</jats:italic>‐Mannich reactions. Additionally, both <jats:italic>N</jats:italic>‐tosyl and <jats:italic>N</jats:italic>‐nosyl imines can be successfully used and the Mannich adducts can be easily reduced or oxidized, and after <jats:italic>N</jats:italic>‐deprotection the corresponding β‐amino acids and β‐amino alcohols can be obtained with good yields. The results also show that this ternary catalytic system may be practical in other enamine‐based reactions.</jats:p>"}]}],"creator":[{"@id":"https://cir.nii.ac.jp/crid/1380298344648469504","@type":"Researcher","foaf:name":[{"@value":"Enrique Gómez‐Bengoa"}]},{"@id":"https://cir.nii.ac.jp/crid/1382262946352273796","@type":"Researcher","foaf:name":[{"@value":"Miguel Maestro"}]},{"@id":"https://cir.nii.ac.jp/crid/1382262946352273794","@type":"Researcher","foaf:name":[{"@value":"Antonia Mielgo"}]},{"@id":"https://cir.nii.ac.jp/crid/1382262946352273795","@type":"Researcher","foaf:name":[{"@value":"Itziar Otazo"}]},{"@id":"https://cir.nii.ac.jp/crid/1382262946352273797","@type":"Researcher","foaf:name":[{"@value":"Claudio Palomo"}]},{"@id":"https://cir.nii.ac.jp/crid/1382262946352273793","@type":"Researcher","foaf:name":[{"@value":"Irene Velilla"}]}],"publication":{"publicationIdentifier":[{"@type":"PISSN","@value":"09476539"},{"@type":"EISSN","@value":"15213765"}],"prism:publicationName":[{"@value":"Chemistry – A European Journal"}],"dc:publisher":[{"@value":"Wiley"}],"prism:publicationDate":"2010-05-04","prism:volume":"16","prism:number":"18","prism:startingPage":"5333","prism:endingPage":"5342"},"reviewed":"false","dc:rights":["http://onlinelibrary.wiley.com/termsAndConditions#vor"],"url":[{"@id":"https://api.wiley.com/onlinelibrary/tdm/v1/articles/10.1002%2Fchem.200903537"},{"@id":"https://chemistry-europe.onlinelibrary.wiley.com/doi/pdf/10.1002/chem.200903537"}],"createdAt":"2010-03-22","modifiedAt":"2025-10-12","relatedProduct":[{"@id":"https://cir.nii.ac.jp/crid/1360004239761113600","@type":"Article","resourceType":"学術雑誌論文(journal article)","relationType":["isReferencedBy"],"jpcoar:relatedTitle":[{"@value":"NaHSO3-Promoted Ring Openings of N-Tosylaziridines and Epoxides with H2O"}]},{"@id":"https://cir.nii.ac.jp/crid/1360565164418903680","@type":"Article","resourceType":"学術雑誌論文(journal article)","relationType":["isReferencedBy"],"jpcoar:relatedTitle":[{"@value":"One‐Pot Synthesis of Chiral Aziridines by a Domino Reaction by Using Desulfonylative Formation on the <i>N</i>‐Tosyl Imine of Chloroacetaldehyde with an Asymmetric Mannich Reaction as a Key Step"}]},{"@id":"https://cir.nii.ac.jp/crid/1360567183167217536","@type":"Article","resourceType":"学術雑誌論文(journal article)","relationType":["isReferencedBy"],"jpcoar:relatedTitle":[{"@value":"Mechanistic Studies of Highly Enantio- and Diastereoselective Aza-Petasis–Ferrier Rearrangement Catalyzed by Chiral Phosphoric Acid"}]},{"@id":"https://cir.nii.ac.jp/crid/1360567183183302272","@type":"Article","resourceType":"学術雑誌論文(journal article)","relationType":["isReferencedBy"],"jpcoar:relatedTitle":[{"@value":"Asymmetric Synthesis and Catalytic Activity of 3-Methyl-β-proline in Enantioselective <i>anti</i>-Mannich-type Reactions"}]},{"@id":"https://cir.nii.ac.jp/crid/1360846639395572096","@type":"Article","resourceType":"学術雑誌論文(journal article)","relationType":["isReferencedBy"],"jpcoar:relatedTitle":[{"@value":"Asymmetric Mannich Reaction of Imines Derived from Aliphatic and Aromatic Aldehydes Catalyzed by Diarylprolinol Silyl Ether"}]},{"@id":"https://cir.nii.ac.jp/crid/1390001205340166400","@type":"Article","resourceType":"学術雑誌論文(journal article)","relationType":["isReferencedBy"],"jpcoar:relatedTitle":[{"@language":"en","@value":"The Asymmetric Catalytic Mannich Reaction Catalyzed by Organocatalyst — A Personal Account —"},{"@value":"The Asymmetric Catalytic Mannich Reaction Catalyzed by Organocatalyst : A Personal Account"},{"@value":"The Asymmetric Catalytic Mannich Reaction Catalyzed by Organocatalyst ^|^mdash; A Personal Account ^|^mdash;"},{"@value":"ChemInform Abstract: The Asymmetric Catalytic Mannich Reaction Catalyzed by Organocatalyst: a Personal Account"}]},{"@id":"https://cir.nii.ac.jp/crid/1390282679150050048","@type":"Article","relationType":["isReferencedBy"],"jpcoar:relatedTitle":[{"@language":"en","@value":"Silica-Supported Boric Acid with Ionic Liquid: A Novel Recyclable Catalytic System for One-Pot Three-Component Mannich Reaction"}]}],"dataSourceIdentifier":[{"@type":"CROSSREF","@value":"10.1002/chem.200903537"},{"@type":"CROSSREF","@value":"10.1248/cpb.59.639_references_DOI_FrTAPhk40wwHYwLuMRcNXhcky3h"},{"@type":"CROSSREF","@value":"10.1002/chem.201101668_references_DOI_FrTAPhk40wwHYwLuMRcNXhcky3h"},{"@type":"CROSSREF","@value":"10.5059/yukigoseikyokaishi.72.1228_references_DOI_FrTAPhk40wwHYwLuMRcNXhcky3h"},{"@type":"CROSSREF","@value":"10.1002/chem.201101077_references_DOI_FrTAPhk40wwHYwLuMRcNXhcky3h"},{"@type":"CROSSREF","@value":"10.3987/com-13-12885_references_DOI_FrTAPhk40wwHYwLuMRcNXhcky3h"},{"@type":"CROSSREF","@value":"10.1021/ja5017206_references_DOI_FrTAPhk40wwHYwLuMRcNXhcky3h"},{"@type":"CROSSREF","@value":"10.1021/jo4010316_references_DOI_FrTAPhk40wwHYwLuMRcNXhcky3h"}]}