DC Field | Value | Language |
---|---|---|
dc.contributor.author | Kim, Suhyeon | ko |
dc.contributor.author | Song, Se Lin | ko |
dc.contributor.author | Zhang, Jianbo | ko |
dc.contributor.author | Kim, Dongwook | ko |
dc.contributor.author | Hong, Sungwoo | ko |
dc.contributor.author | Chang, Sukbok | ko |
dc.date.accessioned | 2023-08-09T01:01:46Z | - |
dc.date.available | 2023-08-09T01:01:46Z | - |
dc.date.created | 2023-08-07 | - |
dc.date.issued | 2023-07 | - |
dc.identifier.citation | JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, v.145, no.29, pp.16238 - 16248 | - |
dc.identifier.issn | 0002-7863 | - |
dc.identifier.uri | http://hdl.handle.net/10203/311287 | - |
dc.description.abstract | Controlling 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.language | English | - |
dc.publisher | AMER CHEMICAL SOC | - |
dc.title | Regio- and Enantioselective Catalytic δ-C-H Amidation of Dioxazolones Enabled by Open-Shell Copper-Nitrenoid Transfer | - |
dc.type | Article | - |
dc.identifier.wosid | 001031282600001 | - |
dc.identifier.scopusid | 2-s2.0-85165778364 | - |
dc.type.rims | ART | - |
dc.citation.volume | 145 | - |
dc.citation.issue | 29 | - |
dc.citation.beginningpage | 16238 | - |
dc.citation.endingpage | 16248 | - |
dc.citation.publicationname | JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | - |
dc.identifier.doi | 10.1021/jacs.3c05258 | - |
dc.contributor.localauthor | Hong, Sungwoo | - |
dc.contributor.localauthor | Chang, Sukbok | - |
dc.contributor.nonIdAuthor | Zhang, Jianbo | - |
dc.description.isOpenAccess | N | - |
dc.type.journalArticle | Article | - |
dc.subject.keywordPlus | C-H AMINATION | - |
dc.subject.keywordPlus | GAMMA-LACTAMS | - |
dc.subject.keywordPlus | DELTA | - |
dc.subject.keywordPlus | PIPERIDINE | - |
dc.subject.keywordPlus | REACTIVITY | - |
dc.subject.keywordPlus | ACCESS | - |
dc.subject.keywordPlus | COMPLEXES | - |
dc.subject.keywordPlus | STRATEGY | - |
dc.subject.keywordPlus | BONDS | - |
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