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Stereodefined Access to Lactams via Olefin Difunctionalization: Iridium Nitrenoids as a Motif of LUMO-Controlled Dipoles
DC Field | Value | Language |
---|---|---|
dc.contributor.author | Hong, Seung Youn | - |
dc.contributor.author | Chang, Sukbok | - |
dc.date.accessioned | 2023-05-03T07:46:42Z | - |
dc.date.available | 2023-05-03T07:46:42Z | - |
dc.date.created | 2023-05-02 | - |
dc.date.created | 2023-05-02 | - |
dc.date.issued | 2019-07 | - |
dc.identifier.citation | Journal of the American Chemical Society, Vol.141 No.26, pp.10399-10408 | - |
dc.identifier.issn | 0002-7863 | - |
dc.identifier.uri | https://hdl.handle.net/10371/191837 | - |
dc.description.abstract | Reported herein is a general platform of a stereodefined access to gamma-lactams via Cp*Ir-catalyzed olefin difunctionalization, where in situ generated Ir-nitrenoid is utilized as a key motif of 1,3-dipoles to enable amido transfer in a syn-selective manner. Computational studies suggested that the stereodefined process can be attributed to the proposed working mode of concerted [3 + 2] cyclization. Frontier molecular orbital (FMO) analysis implied that a low-lying lowest unoccupied molecular orbital (LUMO) of the Ir-imido fragment engages in the olefin interaction. Mechanistic understanding on the nitrene transfer process led us to develop mild catalytic protocols of stereoselective difunctionalization of alkenyl dioxazolones to furnish alpha-(haloalkyl)- or (oxyalkyl)lactam products which are of high synthetic and medicinal utility. Product stereochemistry (threo and erythro) was found to be designated by the olefin geometry (E/Z) of substrates. | - |
dc.language | 영어 | - |
dc.publisher | American Chemical Society | - |
dc.title | Stereodefined Access to Lactams via Olefin Difunctionalization: Iridium Nitrenoids as a Motif of LUMO-Controlled Dipoles | - |
dc.type | Article | - |
dc.identifier.doi | 10.1021/jacs.9b04317 | - |
dc.citation.journaltitle | Journal of the American Chemical Society | - |
dc.identifier.wosid | 000474669700034 | - |
dc.identifier.scopusid | 2-s2.0-85068337895 | - |
dc.citation.endpage | 10408 | - |
dc.citation.number | 26 | - |
dc.citation.startpage | 10399 | - |
dc.citation.volume | 141 | - |
dc.description.isOpenAccess | N | - |
dc.contributor.affiliatedAuthor | Hong, Seung Youn | - |
dc.type.docType | Article | - |
dc.description.journalClass | 1 | - |
dc.subject.keywordPlus | C-H ACTIVATION | - |
dc.subject.keywordPlus | 1,3-DIPOLAR CYCLOADDITIONS | - |
dc.subject.keywordPlus | VICINAL OXYAMINATION | - |
dc.subject.keywordPlus | NITROGEN-SOURCE | - |
dc.subject.keywordPlus | AMINOHYDROXYLATION | - |
dc.subject.keywordPlus | AZIRIDINATION | - |
dc.subject.keywordPlus | ALKENES | - |
dc.subject.keywordPlus | DIAMINATION | - |
dc.subject.keywordPlus | REACTIVITY | - |
dc.subject.keywordPlus | AMINATION | - |
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