{"@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/1050869456404201216.json","@type":"Article","productIdentifier":[{"identifier":{"@type":"HDL","@value":"https://hdl.handle.net/2115/86602"}},{"identifier":{"@type":"DOI","@value":"10.1021/jacs.1c06538"}},{"identifier":{"@type":"URI","@value":"https://pubs.acs.org/doi/pdf/10.1021/jacs.1c06538"}},{"identifier":{"@type":"PMID","@value":"34424698"}},{"identifier":{"@type":"HANDLE","@value":"2115/86602"}}],"resourceType":"学術雑誌論文(journal article)","dc:title":[{"@language":"en","@value":"Regio- and Stereoselective Synthesis of Multi-Alkylated Allylic Boronates through Three-Component Coupling Reactions between Allenes, Alkyl Halides, and a Diboron Reagent"}],"dc:language":"en","description":[{"type":"Abstract","notation":[{"@language":"en","@value":"Multisubstituted allylic boronates are attractive and valuable precursors for the rapid and stereoselective construction of densely substituted carbon skeletons. Herein, we report the first synthetic approach for differentially 2,3,3-triallcyl-substituted allylic boronates that contain a stereodefined tetrasubstituted alkene structure. Copper(I)-catalyzed regio- and stereoselective three-component coupling reactions between gem-dialkylallenes, alkyl halides, and a diboron reagent afforded sterically congested allylic boronates. The allylboration of aldehydes diastereoselectively furnished the corresponding homoallylic alcohols that bear a quaternary carbon. A computational study revealed that the selectivity-determining mechanism was correlated to the coordination of a boryl copper(I) species to the allene substrate as well as the borylcupration step."}]}],"creator":[{"@id":"https://cir.nii.ac.jp/crid/1070587981427639555","@type":"Researcher","personIdentifier":[{"@type":"NRID","@value":"9000402607421"},{"@type":"RESEARCHMAP","@value":"https://researchmap.jp/ozawa_yu"}],"foaf:name":[{"@language":"en","@value":"Ozawa, Yu"}]},{"@id":"https://cir.nii.ac.jp/crid/1420282801213618816","@type":"Researcher","personIdentifier":[{"@type":"KAKEN_RESEARCHERS","@value":"90282300"},{"@type":"NRID","@value":"1000090282300"},{"@type":"NRID","@value":"9000322680253"},{"@type":"NRID","@value":"9000325832090"},{"@type":"NRID","@value":"9000297476329"},{"@type":"NRID","@value":"9000290381592"},{"@type":"NRID","@value":"9000340953306"},{"@type":"NRID","@value":"9000410483971"},{"@type":"NRID","@value":"9000394470609"},{"@type":"NRID","@value":"9000256014196"},{"@type":"NRID","@value":"9000256904753"},{"@type":"NRID","@value":"9000340952972"},{"@type":"NRID","@value":"9000376926832"},{"@type":"NRID","@value":"9000018804751"},{"@type":"NRID","@value":"9000282391310"},{"@type":"NRID","@value":"9000405662212"},{"@type":"NRID","@value":"9000403269726"},{"@type":"NRID","@value":"9000375921390"},{"@type":"NRID","@value":"9000001729414"},{"@type":"NRID","@value":"9000002009738"},{"@type":"NRID","@value":"9000340465289"},{"@type":"NRID","@value":"9000351082811"},{"@type":"NRID","@value":"9000406227564"},{"@type":"NRID","@value":"9000414501359"},{"@type":"NRID","@value":"9000409205516"},{"@type":"NRID","@value":"9000366505306"},{"@type":"NRID","@value":"9000402607423"},{"@type":"NRID","@value":"9000399545105"},{"@type":"NRID","@value":"9000402940183"},{"@type":"NRID","@value":"9000257711498"},{"@type":"NRID","@value":"9000367020552"},{"@type":"NRID","@value":"9000000032925"},{"@type":"NRID","@value":"9000324642488"},{"@type":"NRID","@value":"9000242124768"},{"@type":"NRID","@value":"9000274300526"},{"@type":"NRID","@value":"9000392826707"},{"@type":"NRID","@value":"9000398788688"},{"@type":"NRID","@value":"9000256904811"},{"@type":"NRID","@value":"9000413495525"},{"@type":"NRID","@value":"9000326661629"},{"@type":"NRID","@value":"9000404633807"},{"@type":"NRID","@value":"9000410310209"},{"@type":"NRID","@value":"9000000552016"},{"@type":"NRID","@value":"9000411586854"},{"@type":"NRID","@value":"9000410147744"},{"@type":"NRID","@value":"9000411768090"},{"@type":"NRID","@value":"9000005331717"},{"@type":"NRID","@value":"9000018165140"},{"@type":"NRID","@value":"9000294355842"},{"@type":"NRID","@value":"9000356913427"},{"@type":"NRID","@value":"9000402913190"},{"@type":"NRID","@value":"9000411514448"},{"@type":"NRID","@value":"9000237783272"},{"@type":"NRID","@value":"9000339140497"},{"@type":"NRID","@value":"9000286276837"},{"@type":"NRID","@value":"9000411277302"},{"@type":"NRID","@value":"9000362202804"},{"@type":"NRID","@value":"9000368412104"},{"@type":"NRID","@value":"9000402100559"},{"@type":"NRID","@value":"9000392860619"},{"@type":"NRID","@value":"9000255702094"},{"@type":"NRID","@value":"9000257710922"},{"@type":"NRID","@value":"9000005333031"},{"@type":"NRID","@value":"9000404660895"},{"@type":"NRID","@value":"9000409497233"},{"@type":"NRID","@value":"9000406225598"},{"@type":"NRID","@value":"9000379609827"},{"@type":"NRID","@value":"9000283624083"},{"@type":"NRID","@value":"9000001800923"},{"@type":"NRID","@value":"9000414724970"},{"@type":"NRID","@value":"9000305642796"},{"@type":"NRID","@value":"9000411248872"},{"@type":"NRID","@value":"9000397968734"},{"@type":"NRID","@value":"9000380962833"},{"@type":"NRID","@value":"9000412229672"},{"@type":"NRID","@value":"9000396162690"},{"@type":"NRID","@value":"9000412336167"},{"@type":"NRID","@value":"9000412336135"},{"@type":"NRID","@value":"9000250177877"},{"@type":"NRID","@value":"9000343344163"},{"@type":"NRID","@value":"9000346963720"},{"@type":"NRID","@value":"9000296666662"},{"@type":"NRID","@value":"9000293532097"},{"@type":"NRID","@value":"9000381958609"},{"@type":"NRID","@value":"9000365620497"},{"@type":"NRID","@value":"9000257726107"},{"@type":"NRID","@value":"9000018773674"},{"@type":"NRID","@value":"9000410036165"},{"@type":"NRID","@value":"9000398646468"},{"@type":"NRID","@value":"9000398303558"},{"@type":"NRID","@value":"9000408784107"},{"@type":"NRID","@value":"9000409331694"},{"@type":"NRID","@value":"9000288816804"},{"@type":"RESEARCHMAP","@value":"https://researchmap.jp/read0103056"}],"foaf:name":[{"@language":"en","@value":"Ito, Hajime"}]},{"@id":"https://cir.nii.ac.jp/crid/1070869456404201218","@type":"Researcher","foaf:name":[{"@language":"en","@value":"Endo, Kohei"}]}],"publication":{"publicationIdentifier":[{"@type":"PISSN","@value":"00027863"},{"@type":"EISSN","@value":"15205126"}],"prism:publicationName":[{"@language":"en","@value":"Journal of the American Chemical Society"}],"dc:publisher":[{"@value":"American Chemical Society"}],"prism:publicationDate":"2021-09-01","prism:volume":"143","prism:number":"34","prism:startingPage":"13865","prism:endingPage":"13877"},"reviewed":"false","dcterms:accessRights":"http://purl.org/coar/access_right/c_abf2","dc:rights":["This document is the Accepted Manuscript version of a Published Work that appeared in final form in Journal of the American Chemical Society, copyright c American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see https://pubs.acs.org/articlesonrequest/AOR-QNGFNQYSKV5ZNX5JW8EP."],"url":[{"@id":"https://pubs.acs.org/doi/pdf/10.1021/jacs.1c06538"}],"foaf:topic":[{"@id":"https://cir.nii.ac.jp/all?q=Multi-substituted%20allylic%20boronates","dc:title":"Multi-substituted allylic boronates"},{"@id":"https://cir.nii.ac.jp/all?q=Carboboration%20recation","dc:title":"Carboboration recation"},{"@id":"https://cir.nii.ac.jp/all?q=Copper(I)%20catalyst","dc:title":"Copper(I) catalyst"},{"@id":"https://cir.nii.ac.jp/all?q=DFT%20calculation","dc:title":"DFT calculation"}],"dcterms:subject":[{"subjectScheme":"Other","notation":[{"@language":"en","@value":"Multi-substituted allylic boronates"}]},{"subjectScheme":"Other","notation":[{"@language":"en","@value":"Carboboration recation"}]},{"subjectScheme":"Other","notation":[{"@language":"en","@value":"Copper(I) catalyst"}]},{"subjectScheme":"Other","notation":[{"@language":"en","@value":"DFT calculation"}]}],"project":[{"@id":"https://cir.nii.ac.jp/crid/1040000781994186240","@type":"Project","projectIdentifier":[{"@type":"KAKEN","@value":"18H03907"},{"@type":"JGN","@value":"JP18H03907"},{"@type":"URI","@value":"https://kaken.nii.ac.jp/grant/KAKENHI-PROJECT-18H03907/"}],"notation":[{"@language":"ja","@value":"非対称稠密反応空間による不斉ホウ素化"},{"@language":"en","@value":"Asymmetric Borylation with Chiral Dense Reaction Space"}]},{"@id":"https://cir.nii.ac.jp/crid/1040848250604072192","@type":"Project","projectIdentifier":[{"@type":"KAKEN","@value":"19J20823"},{"@type":"JGN","@value":"JP19J20823"},{"@type":"URI","@value":"https://kaken.nii.ac.jp/grant/KAKENHI-PROJECT-19J20823/"}],"notation":[{"@language":"ja","@value":"光学活性有機銅(III)を活用した新規触媒的不斉ホウ素化反応の開発"}]}],"relatedProduct":[{"@id":"https://cir.nii.ac.jp/crid/1050306506449625984","@type":"Article","resourceType":"学術雑誌論文(journal article)","relationType":["isReferencedBy"],"jpcoar:relatedTitle":[{"@language":"en","@value":"Ring Expansion of 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