{"@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/1361699996322966528.json","@type":"Article","productIdentifier":[{"identifier":{"@type":"DOI","@value":"10.1002/anie.201903455"}},{"identifier":{"@type":"URI","@value":"https://api.wiley.com/onlinelibrary/tdm/v1/articles/10.1002%2Fanie.201903455"}},{"identifier":{"@type":"URI","@value":"https://onlinelibrary.wiley.com/doi/pdf/10.1002/anie.201903455"}},{"identifier":{"@type":"URI","@value":"https://onlinelibrary.wiley.com/doi/full-xml/10.1002/anie.201903455"}},{"identifier":{"@type":"URI","@value":"https://onlinelibrary.wiley.com/doi/am-pdf/10.1002/anie.201903455"}}],"dc:title":[{"@value":"Biocatalytic Strategy for Highly Diastereo‐ and Enantioselective Synthesis of 2,3‐Dihydrobenzofuran‐Based Tricyclic Scaffolds"}],"description":[{"type":"abstract","notation":[{"@value":"<jats:title>Abstract</jats:title><jats:p>2,3‐Dihydrobenzofurans are key pharmacophores in many natural and synthetic bioactive molecules. A biocatalytic strategy is reported here for the highly diastereo‐ and enantioselective construction of stereochemically rich 2,3‐dihydrobenzofurans in high enantiopurity (>99.9% de and ee), high yields, and on a preparative scale via benzofuran cyclopropanation with engineered myoglobins. Computational and structure‐reactivity studies provide insights into the mechanism of this reaction, enabling the elaboration of a stereochemical model that can rationalize the high stereoselectivity of the biocatalyst. This information was leveraged to implement a highly stereoselective route to a drug molecule and a tricyclic scaffold featuring five stereogenic centers via a single‐enzyme transformation. This work expands the biocatalytic toolbox for asymmetric C–C bond transformations and should prove useful for further development of metalloprotein catalysts for abiotic carbene transfer reactions.</jats:p>"}]}],"creator":[{"@id":"https://cir.nii.ac.jp/crid/1381699996322966529","@type":"Researcher","foaf:name":[{"@value":"David A. Vargas"}],"jpcoar:affiliationName":[{"@value":"Department of Chemistry University of Rochester  120 Trustee Road Rochester NY 14627 USA"}]},{"@id":"https://cir.nii.ac.jp/crid/1381699996322966530","@type":"Researcher","foaf:name":[{"@value":"Rahul L. Khade"}],"jpcoar:affiliationName":[{"@value":"Department of Chemistry and Chemical Biology Stevens Institute of Technology  Hoboken NJ 07030 USA"}]},{"@id":"https://cir.nii.ac.jp/crid/1381699996322966528","@type":"Researcher","foaf:name":[{"@value":"Yong Zhang"}],"jpcoar:affiliationName":[{"@value":"Department of Chemistry and Chemical Biology Stevens Institute of Technology  Hoboken NJ 07030 USA"}]},{"@id":"https://cir.nii.ac.jp/crid/1381699996322966531","@type":"Researcher","foaf:name":[{"@value":"Rudi Fasan"}],"jpcoar:affiliationName":[{"@value":"Department of Chemistry University of Rochester  120 Trustee Road Rochester NY 14627 USA"}]}],"publication":{"publicationIdentifier":[{"@type":"PISSN","@value":"14337851"},{"@type":"EISSN","@value":"15213773"}],"prism:publicationName":[{"@value":"Angewandte Chemie International Edition"}],"dc:publisher":[{"@value":"Wiley"}],"prism:publicationDate":"2019-06-24","prism:volume":"58","prism:number":"30","prism:startingPage":"10148","prism:endingPage":"10152"},"reviewed":"false","dc:rights":["http://onlinelibrary.wiley.com/termsAndConditions#am","http://onlinelibrary.wiley.com/termsAndConditions#vor"],"url":[{"@id":"https://api.wiley.com/onlinelibrary/tdm/v1/articles/10.1002%2Fanie.201903455"},{"@id":"https://onlinelibrary.wiley.com/doi/pdf/10.1002/anie.201903455"},{"@id":"https://onlinelibrary.wiley.com/doi/full-xml/10.1002/anie.201903455"},{"@id":"https://onlinelibrary.wiley.com/doi/am-pdf/10.1002/anie.201903455"}],"createdAt":"2019-05-17","modifiedAt":"2023-09-08","relatedProduct":[{"@id":"https://cir.nii.ac.jp/crid/1050581168899666944","@type":"Article","resourceType":"学術雑誌論文(journal article)","relationType":["isReferencedBy"],"jpcoar:relatedTitle":[{"@language":"en","@value":"Chitin- and Streptavidin- Mediated Affinity Purification Systems: A Screening Platform for Enzyme Discovery"},{"@value":"Chitin‐ and Streptavidin‐Mediated Affinity Purification Systems: A Screening Platform for Enzyme Discovery"}]},{"@id":"https://cir.nii.ac.jp/crid/1360572092786604928","@type":"Article","resourceType":"学術雑誌論文(journal article)","relationType":["isReferencedBy"],"jpcoar:relatedTitle":[{"@value":"Enhanced\n                    <i>cis</i>\n                    - and enantioselective cyclopropanation of styrene catalysed by cytochrome P450BM3 using decoy molecules"}]},{"@id":"https://cir.nii.ac.jp/crid/1390576282600090240","@type":"Article","relationType":["isReferencedBy"],"jpcoar:relatedTitle":[{"@language":"en","@value":"Engineered Myoglobin Catalysts for Asymmetric Intermolecular Cyclopropanation Reactions"}]},{"@id":"https://cir.nii.ac.jp/crid/2050870367081136768","@type":"Article","relationType":["isReferencedBy"],"jpcoar:relatedTitle":[{"@value":"Exploring and adapting the molecular selectivity of artificial metalloenzymes"}]}],"dataSourceIdentifier":[{"@type":"CROSSREF","@value":"10.1002/anie.201903455"},{"@type":"CROSSREF","@value":"10.1002/anie.202303764_references_DOI_GptnoLueiBfMSyezTHPsNMot4b6"},{"@type":"CROSSREF","@value":"10.1246/bcsj.20200316_references_DOI_GptnoLueiBfMSyezTHPsNMot4b6"},{"@type":"CROSSREF","@value":"10.1039/d0cc04883f_references_DOI_GptnoLueiBfMSyezTHPsNMot4b6"},{"@type":"CROSSREF","@value":"10.4019/bjscc.80.4_references_DOI_GptnoLueiBfMSyezTHPsNMot4b6"},{"@type":"CROSSREF","@value":"10.1002/ange.202303764_references_DOI_GptnoLueiBfMSyezTHPsNMot4b6"}]}