Allylic Acetals as Acrolein Oxonium Precursors in Tandem C-H Allylation and [3+2] Dipolar Cycloaddition

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dc.contributor.authorLee, Heeyoungko
dc.contributor.authorKang, Dahyeko
dc.contributor.authorHan, Sang Hoonko
dc.contributor.authorChun, Rinako
dc.contributor.authorPandey, Ashok Kumarko
dc.contributor.authorMishra, Neeraj Kumarko
dc.contributor.authorHong, Sungwooko
dc.contributor.authorKim, In Suko
dc.date.accessioned2019-08-05T07:20:26Z-
dc.date.available2019-08-05T07:20:26Z-
dc.date.created2019-08-05-
dc.date.created2019-08-05-
dc.date.created2019-08-05-
dc.date.issued2019-07-
dc.identifier.citationANGEWANDTE CHEMIE-INTERNATIONAL EDITION, v.58, no.28, pp.9470 - 9474-
dc.identifier.issn1433-7851-
dc.identifier.urihttp://hdl.handle.net/10203/264008-
dc.description.abstractThe ruthenium(II)-catalyzed C-H functionalization of (hetero)aryl azomethine imines with allylic acetals is described. The initial formation of allylidene(methyl)oxoniums from allylic acetals could trigger C(sp(2))-H allylation, and subsequent endo-type [3+2] dipolar cycloaddition of polar azomethine fragments to deliver valuable indenopyrazolopyrazolones. The utility of this method is showcased by the late-stage functionalization of bioactive molecules such as estrone and celecoxib. Combined experimental and computational investigations elucidate a plausible mechanism of this new tandem reaction. Notably, the reductive transformation of synthesized compounds into biologically relevant diazocine frameworks highlights the importance of the developed methodology.-
dc.languageEnglish-
dc.publisherWILEY-V C H VERLAG GMBH-
dc.titleAllylic Acetals as Acrolein Oxonium Precursors in Tandem C-H Allylation and [3+2] Dipolar Cycloaddition-
dc.typeArticle-
dc.identifier.wosid000476610900025-
dc.identifier.scopusid2-s2.0-85066999897-
dc.type.rimsART-
dc.citation.volume58-
dc.citation.issue28-
dc.citation.beginningpage9470-
dc.citation.endingpage9474-
dc.citation.publicationnameANGEWANDTE CHEMIE-INTERNATIONAL EDITION-
dc.identifier.doi10.1002/anie.201903983-
dc.contributor.localauthorHong, Sungwoo-
dc.contributor.nonIdAuthorLee, Heeyoung-
dc.contributor.nonIdAuthorHan, Sang Hoon-
dc.contributor.nonIdAuthorChun, Rina-
dc.contributor.nonIdAuthorPandey, Ashok Kumar-
dc.contributor.nonIdAuthorMishra, Neeraj Kumar-
dc.contributor.nonIdAuthorKim, In Su-
dc.description.isOpenAccessN-
dc.type.journalArticleArticle-
dc.subject.keywordAuthorallylic acetal-
dc.subject.keywordAuthorC-H functionalization-
dc.subject.keywordAuthordipolar cycloaddition-
dc.subject.keywordAuthorindenopyrazolopyrazolone-
dc.subject.keywordAuthortandem reaction-
dc.subject.keywordPlus1,3-DIPOLAR CYCLOADDITION-
dc.subject.keywordPlusAZOMETHINE IMINES-
dc.subject.keywordPlusBOND ACTIVATION-
dc.subject.keywordPlusFUNCTIONALIZATION-
dc.subject.keywordPlusALKENES-
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