DC Field | Value | Language |
---|---|---|
dc.contributor.author | Lee, Wooseok | ko |
dc.contributor.author | Koo, Yejin | ko |
dc.contributor.author | Jung, Hoimin | ko |
dc.contributor.author | Chang, Sukbok | ko |
dc.contributor.author | Hong, Sungwoo | ko |
dc.date.accessioned | 2023-08-04T02:00:23Z | - |
dc.date.available | 2023-08-04T02:00:23Z | - |
dc.date.created | 2023-07-31 | - |
dc.date.created | 2023-07-31 | - |
dc.date.issued | 2023-06 | - |
dc.identifier.citation | NATURE CHEMISTRY, v.15, no.8, pp.1091 - 1099 | - |
dc.identifier.issn | 1755-4330 | - |
dc.identifier.uri | http://hdl.handle.net/10203/311151 | - |
dc.description.abstract | Photocycloaddition is a powerful reaction to enable the conversion of alkenes into high-value synthetic materials that are normally difficult to obtain under thermal conditions. Lactams and pyridines, both prominent in pharmaceutical applications, currently lack effective synthetic strategies to combine them within a single molecular structure. Here we describe an efficient approach to diastereoselective pyridyl lactamization via a photoinduced [3+2] cycloaddition, based on the unique triplet-state reactivity of N-N pyridinium ylides in the presence of a photosensitizer. The corresponding triplet diradical intermediates allow the stepwise radical [3+2] cycloaddition with a broad range of activated and unactivated alkenes under mild conditions. This method exhibits excellent efficiency, diastereoselectivity and functional group tolerance, providing a useful synthon for ortho-pyridyl ?- and d-lactam scaffolds with syn-configuration in a single step. Combined experimental and computational studies reveal that the energy transfer process leads to a triplet-state diradical of N-N pyridinium ylides, which promotes the stepwise cycloaddition. | - |
dc.language | English | - |
dc.publisher | NATURE PORTFOLIO | - |
dc.title | Energy-transfer-induced [3+2] cycloadditions of N-N pyridinium ylides | - |
dc.type | Article | - |
dc.identifier.wosid | 001020380800002 | - |
dc.identifier.scopusid | 2-s2.0-85162846337 | - |
dc.type.rims | ART | - |
dc.citation.volume | 15 | - |
dc.citation.issue | 8 | - |
dc.citation.beginningpage | 1091 | - |
dc.citation.endingpage | 1099 | - |
dc.citation.publicationname | NATURE CHEMISTRY | - |
dc.identifier.doi | 10.1038/s41557-023-01258-2 | - |
dc.contributor.localauthor | Chang, Sukbok | - |
dc.contributor.localauthor | Hong, Sungwoo | - |
dc.description.isOpenAccess | N | - |
dc.type.journalArticle | Article | - |
dc.subject.keywordPlus | CENTERED RADICALS | - |
dc.subject.keywordPlus | LIGHT | - |
dc.subject.keywordPlus | PHOTOCATALYSIS | - |
dc.subject.keywordPlus | PRECURSORS | - |
dc.subject.keywordPlus | GENERATION | - |
dc.subject.keywordPlus | ACCESS | - |
dc.subject.keywordPlus | ARENES | - |
dc.subject.keywordPlus | SALTS | - |
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