Decarboxylative stereoretentive C–N coupling by harnessing aminating reagent
DC Field | Value | Language |
---|---|---|
dc.contributor.author | Jeonguk Kweon | - |
dc.contributor.author | Park, Bumsu | - |
dc.contributor.author | Dongwook Kim | - |
dc.contributor.author | Sukbok Chang | - |
dc.date.accessioned | 2024-05-17T05:30:02Z | - |
dc.date.available | 2024-05-17T05:30:02Z | - |
dc.date.created | 2024-05-13 | - |
dc.date.issued | 2024 | - |
dc.identifier.uri | https://pr.ibs.re.kr/handle/8788114/15153 | - |
dc.description.abstract | In recent decades, strategies involving transition-metal catalyzed carbon-carbon or carbon-heteroatom bond coupling have emerged as potent synthetic tools for constructing intricate molecular architectures. Among these, decarboxylative carbon-nitrogen bond formation using abundant carboxylic acids or their derivatives has garnered notable attention for accessing alkyl- or arylamines, one of key pharmacophores. While several decarboxylative amination methods have been developed, the involvement of a common carboradical intermediate currently poses challenges in achieving stereospecific transformation toward chiral alkylamines. Herein, we present a base-mediated, stereoretentive decarboxylative amidation by harnessing 1,4,2-dioxazol-5-one as a reactive and robust amidating reagent under transition-metal-free ambient conditions, encompassing all types of primary, secondary and tertiary carboxylic acids, thereby providing access to the important pharmacophore, α-chiral amines. This method exhibits high functional group tolerance, convenient scalability, and ease of applicability for 15N-isotope labeling, thus accentuating its synthetic utilities. Experimental and computational mechanistic investigations reveal a sequence of elementary steps: i) nucleophilic addition of carboxylate to dioxazolone, ii) rearrangement to form a dicarbonyl N-hydroxy intermediate, iii) conversion to hydroxamate, followed by a Lossen-type rearrangement, and finally, iv) reaction of the in situ generated isocyanate with carboxylate leading to C–N bond formation in a stereoretentive manner. © The Author(s) 2024. | - |
dc.language | 영어 | - |
dc.publisher | Nature Publishing Group | - |
dc.title | Decarboxylative stereoretentive C–N coupling by harnessing aminating reagent | - |
dc.type | Article | - |
dc.type.rims | ART | - |
dc.identifier.wosid | 001214967700013 | - |
dc.identifier.scopusid | 2-s2.0-85192189982 | - |
dc.identifier.rimsid | 83057 | - |
dc.contributor.affiliatedAuthor | Jeonguk Kweon | - |
dc.contributor.affiliatedAuthor | Dongwook Kim | - |
dc.contributor.affiliatedAuthor | Sukbok Chang | - |
dc.identifier.doi | 10.1038/s41467-024-48075-w | - |
dc.identifier.bibliographicCitation | Nature Communications, v.15, no.1 | - |
dc.relation.isPartOf | Nature Communications | - |
dc.citation.title | Nature Communications | - |
dc.citation.volume | 15 | - |
dc.citation.number | 1 | - |
dc.description.journalClass | 1 | - |
dc.description.journalClass | 1 | - |
dc.description.isOpenAccess | Y | - |
dc.description.journalRegisteredClass | scie | - |
dc.description.journalRegisteredClass | scopus | - |