Au(I)-Catalyzed Hydrative Rearrangement of 1,1-Diethynylcarbinol Acetates to Functionalized Cyclopentenones and Allenones
DC Field | Value | Language |
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dc.contributor.author | Oh, Chang Ho | - |
dc.contributor.author | Karmakar, Swastik | - |
dc.date.accessioned | 2022-12-20T23:52:22Z | - |
dc.date.available | 2022-12-20T23:52:22Z | - |
dc.date.created | 2022-08-26 | - |
dc.date.issued | 2009-01 | - |
dc.identifier.issn | 0022-3263 | - |
dc.identifier.uri | https://scholarworks.bwise.kr/hanyang/handle/2021.sw.hanyang/177434 | - |
dc.description.abstract | Atom-economical syntheses of isomeric 5-acetoxy-2-alkyl-2-cyclopentenones (2) and acetoxymethyl (x-alkylailen ones (3) have been described via Au-catalyzed hydrative rearrangement of 1,1-diethynyl-carbinol acetates (1). In anhydrous condition, Au(I)-catalyzed [3,3]-rearrangement of 1 afforded the 3-alkynylallenyl acetate 4 in low yield. Treatment of 1 with Au(I) catalyst in wet CH2Cl2 produced either 2 or 3 as a major product depending on the temperature, reaction time. and catalyst loading. D has been proposed as an intermediate, which might be formed via Au(I)-induced internal oxacyclization of the intermediate 4 followed by chemoselective nucleophilic attack by the water molecule. Formation of 2 or 3 might be explained via sequential 1,3-dioxole ring opening and gold-promoted 5-endo-dig carbocyclization or simple protonation of the intermediate D, respectively. | - |
dc.language | 영어 | - |
dc.language.iso | en | - |
dc.publisher | AMER CHEMICAL SOC | - |
dc.title | Au(I)-Catalyzed Hydrative Rearrangement of 1,1-Diethynylcarbinol Acetates to Functionalized Cyclopentenones and Allenones | - |
dc.type | Article | - |
dc.contributor.affiliatedAuthor | Oh, Chang Ho | - |
dc.identifier.doi | 10.1021/jo802103g | - |
dc.identifier.scopusid | 2-s2.0-58149311066 | - |
dc.identifier.wosid | 000262004000043 | - |
dc.identifier.bibliographicCitation | JOURNAL OF ORGANIC CHEMISTRY, v.74, no.1, pp.370 - 374 | - |
dc.relation.isPartOf | JOURNAL OF ORGANIC CHEMISTRY | - |
dc.citation.title | JOURNAL OF ORGANIC CHEMISTRY | - |
dc.citation.volume | 74 | - |
dc.citation.number | 1 | - |
dc.citation.startPage | 370 | - |
dc.citation.endPage | 374 | - |
dc.type.rims | ART | - |
dc.type.docType | Article | - |
dc.description.journalClass | 1 | - |
dc.description.isOpenAccess | N | - |
dc.description.journalRegisteredClass | scie | - |
dc.description.journalRegisteredClass | scopus | - |
dc.relation.journalResearchArea | Chemistry | - |
dc.relation.journalWebOfScienceCategory | Chemistry, Organic | - |
dc.subject.keywordPlus | PAUSON-KHAND REACTION | - |
dc.subject.keywordPlus | HIGHLY SUBSTITUTED CYCLOPENTENONES | - |
dc.subject.keywordPlus | EFFICIENT SYNTHESIS | - |
dc.subject.keywordPlus | CATALYZED CYCLOISOMERIZATION | - |
dc.subject.keywordPlus | CARBONYLATIVE CYCLIZATION | - |
dc.subject.keywordPlus | NAZAROV CYCLIZATION | - |
dc.subject.keywordPlus | ORGANIC-SYNTHESIS | - |
dc.subject.keywordPlus | 4+1 CYCLOADDITION | - |
dc.subject.keywordPlus | ENYNYL ACETATES | - |
dc.subject.keywordPlus | ALLENIC KETONES | - |
dc.identifier.url | https://pubs.acs.org/doi/10.1021/jo802103g | - |
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