Double Hydroboration of Quinolines via Borane Catalysis: Diastereoselective One Pot Synthesis of 3-Hydroxytetrahydroquinolines

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dc.contributor.authorKim, Eunaeko
dc.contributor.authorJeon, Hyun Jiko
dc.contributor.authorPark, Sehoonko
dc.contributor.authorChang, Sukbokko
dc.date.accessioned2020-05-14T07:20:15Z-
dc.date.available2020-05-14T07:20:15Z-
dc.date.created2019-10-22-
dc.date.created2019-10-22-
dc.date.issued2020-01-
dc.identifier.citationADVANCED SYNTHESIS & CATALYSIS, v.362, no.2, pp.308 - 313-
dc.identifier.issn1615-4150-
dc.identifier.urihttp://hdl.handle.net/10203/274193-
dc.description.abstractDescribed herein is an organoborane-catalysed consecutive borylative reduction of quinolines and isoquinolines to furnish tetrahydro(iso)quinolines bearing a C(sp(3))-B bond beta to the nitrogen atom. The installed C-B bond is oxidatively transformed to the hydroxy group in one pot. The present double hydroboration is proposed to proceed via a stepwise ionic mechanism involving a boronium ion. The stereo-outcome was found to be dependent on the position (C2 vs C4) of the substituents in quinolines.-
dc.languageEnglish-
dc.publisherWILEY-V C H VERLAG GMBH-
dc.titleDouble Hydroboration of Quinolines via Borane Catalysis: Diastereoselective One Pot Synthesis of 3-Hydroxytetrahydroquinolines-
dc.typeArticle-
dc.identifier.wosid000488580800001-
dc.identifier.scopusid2-s2.0-85074461772-
dc.type.rimsART-
dc.citation.volume362-
dc.citation.issue2-
dc.citation.beginningpage308-
dc.citation.endingpage313-
dc.citation.publicationnameADVANCED SYNTHESIS & CATALYSIS-
dc.identifier.doi10.1002/adsc.201901050-
dc.contributor.localauthorChang, Sukbok-
dc.contributor.nonIdAuthorJeon, Hyun Ji-
dc.contributor.nonIdAuthorPark, Sehoon-
dc.description.isOpenAccessY-
dc.type.journalArticleArticle-
dc.subject.keywordAuthorLewis acidic borane-
dc.subject.keywordAuthorhydroboration-
dc.subject.keywordAuthorconsecutive reaction-
dc.subject.keywordAuthorionic mechanism-
dc.subject.keywordAuthordiastereoselectivity-
dc.subject.keywordPlusASYMMETRIC HYDROGENATION-
dc.subject.keywordPlusSILYLATIVE REDUCTION-
dc.subject.keywordPlusREGIOSELECTIVE 1,4-HYDROBORATION-
dc.subject.keywordPlusN-HETEROARENES-
dc.subject.keywordPlusBORENIUM-
dc.subject.keywordPlusCHEMISTRY-
dc.subject.keywordPlusPYRIDINES-
dc.subject.keywordPlusHYDRIDE-
dc.subject.keywordPlusCARBENE-
dc.subject.keywordPlusPAIRS-
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