Regio- and Enantioselective Catalytic δ-C-H Amidation of Dioxazolones Enabled by Open-Shell Copper-Nitrenoid Transfer

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dc.contributor.authorKim, Suhyeonko
dc.contributor.authorSong, Se Linko
dc.contributor.authorZhang, Jianboko
dc.contributor.authorKim, Dongwookko
dc.contributor.authorHong, Sungwooko
dc.contributor.authorChang, Sukbokko
dc.date.accessioned2023-08-09T01:01:46Z-
dc.date.available2023-08-09T01:01:46Z-
dc.date.created2023-08-07-
dc.date.issued2023-07-
dc.identifier.citationJOURNAL OF THE AMERICAN CHEMICAL SOCIETY, v.145, no.29, pp.16238 - 16248-
dc.identifier.issn0002-7863-
dc.identifier.urihttp://hdl.handle.net/10203/311287-
dc.description.abstractControlling regio- and enantioselectivity in C-Hfunctionalizationreactions is of paramount importance due to their versatile syntheticutilities. Herein, we describe a new approach for the asymmetric & delta;-C(sp(3))-H amidation catalysis of dioxazolones using a Cu(I)precursor with a chiral bisoxazoline ligand to access six-memberedlactams with high to excellent regio- and enantioselectivity (up to>19:1 rr and >99:1 er). Combined experimental and computationalmechanisticstudies unveiled that the open-shell character of the postulated Cu-nitrenoidsenables the regioselective hydrogen atom abstraction and subsequentenantio-determining radical rebound of the resulting carbon radicalintermediates. The synthetic utility of this asymmetric cyclizationwas demonstrated in the diastereoselective introduction of additionalfunctional groups into the chiral & delta;-lactam skeleton as wellas in the rapid access to biorelevant azacyclic compounds.-
dc.languageEnglish-
dc.publisherAMER CHEMICAL SOC-
dc.titleRegio- and Enantioselective Catalytic δ-C-H Amidation of Dioxazolones Enabled by Open-Shell Copper-Nitrenoid Transfer-
dc.typeArticle-
dc.identifier.wosid001031282600001-
dc.identifier.scopusid2-s2.0-85165778364-
dc.type.rimsART-
dc.citation.volume145-
dc.citation.issue29-
dc.citation.beginningpage16238-
dc.citation.endingpage16248-
dc.citation.publicationnameJOURNAL OF THE AMERICAN CHEMICAL SOCIETY-
dc.identifier.doi10.1021/jacs.3c05258-
dc.contributor.localauthorHong, Sungwoo-
dc.contributor.localauthorChang, Sukbok-
dc.contributor.nonIdAuthorZhang, Jianbo-
dc.description.isOpenAccessN-
dc.type.journalArticleArticle-
dc.subject.keywordPlusC-H AMINATION-
dc.subject.keywordPlusGAMMA-LACTAMS-
dc.subject.keywordPlusDELTA-
dc.subject.keywordPlusPIPERIDINE-
dc.subject.keywordPlusREACTIVITY-
dc.subject.keywordPlusACCESS-
dc.subject.keywordPlusCOMPLEXES-
dc.subject.keywordPlusSTRATEGY-
dc.subject.keywordPlusBONDS-
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