DC Field | Value | Language |
---|---|---|
dc.contributor.author | Choi, Hoonchul | ko |
dc.contributor.author | Lyu, Xiang | ko |
dc.contributor.author | Kim, Dongwook | ko |
dc.contributor.author | Seo, Sangwon | ko |
dc.contributor.author | Chang, Sukbok | ko |
dc.date.accessioned | 2022-06-27T09:02:50Z | - |
dc.date.available | 2022-06-27T09:02:50Z | - |
dc.date.created | 2022-06-27 | - |
dc.date.created | 2022-06-27 | - |
dc.date.issued | 2022-06 | - |
dc.identifier.citation | JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, v.144, no.22, pp.10064 - 10074 | - |
dc.identifier.issn | 0002-7863 | - |
dc.identifier.uri | http://hdl.handle.net/10203/297118 | - |
dc.description.abstract | Intramolecular alkyne hydroamidation represents a straightforward approach for the access to synthetically valuable cyclic enamides. Despite some advances made in this realm, the ability to attain a precise regiocontrol still remains challenging, especially for endo cyclization that leads to six-membered and larger azacyclic rings. Herein, we report a NiH-catalyzed intramolecular hydroamidation of alkynyl dioxazolones that allows for an excellent endo selectivity, thus affording a range of six- to eight-membered endocyclic enamides with a broad scope. Mechanistic investigations revealed that Ni(I) catalysis is operative in the current system, proceeding via regioselective syn-hydronickelation, alkenylnickel E/Z isomerization, and Ni-centered inner-sphere nitrenoid transfer. In particular, the key alkenylnickel isomerization step, which previously lacked mechanistic understandings, was found to take place through the 12-vinyl transition state. The synthetic value of this protocol was demonstrated by diastereoselective modifications of the obtained endocyclic enamides to highly functionalized (5-lactam scaffolds. | - |
dc.language | English | - |
dc.publisher | AMER CHEMICAL SOC | - |
dc.title | Endo-Selective Intramolecular Alkyne Hydroamidation Enabled by NiH Catalysis Incorporating Alkenylnickel Isomerization | - |
dc.type | Article | - |
dc.identifier.wosid | 000810029900001 | - |
dc.identifier.scopusid | 2-s2.0-85131771540 | - |
dc.type.rims | ART | - |
dc.citation.volume | 144 | - |
dc.citation.issue | 22 | - |
dc.citation.beginningpage | 10064 | - |
dc.citation.endingpage | 10074 | - |
dc.citation.publicationname | JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | - |
dc.identifier.doi | 10.1021/jacs.2c03777 | - |
dc.contributor.localauthor | Chang, Sukbok | - |
dc.contributor.nonIdAuthor | Lyu, Xiang | - |
dc.contributor.nonIdAuthor | Kim, Dongwook | - |
dc.contributor.nonIdAuthor | Seo, Sangwon | - |
dc.description.isOpenAccess | N | - |
dc.type.journalArticle | Article | - |
dc.subject.keywordPlus | C-H AMIDATION | - |
dc.subject.keywordPlus | CASCADE REACTIONS | - |
dc.subject.keywordPlus | HYDROGEN-BONDS | - |
dc.subject.keywordPlus | AMIDO TRANSFER | - |
dc.subject.keywordPlus | CIS-INSERTION | - |
dc.subject.keywordPlus | GAMMA-LACTAMS | - |
dc.subject.keywordPlus | HYDROAMINATION | - |
dc.subject.keywordPlus | CYCLIZATIONS | - |
dc.subject.keywordPlus | HETEROCYCLES | - |
dc.subject.keywordPlus | COMPLEXES | - |
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