Borane-Catalyzed Reductive alpha-Silylation of Conjugated Esters and Amides Leaving Carbonyl Groups Intact

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dc.contributor.authorKim, Youngchanko
dc.contributor.authorChang, Sukbokko
dc.date.accessioned2016-06-07T09:03:08Z-
dc.date.available2016-06-07T09:03:08Z-
dc.date.created2016-02-12-
dc.date.created2016-02-12-
dc.date.issued2016-01-
dc.identifier.citationANGEWANDTE CHEMIE-INTERNATIONAL EDITION, v.55, no.1, pp.218 - 222-
dc.identifier.issn1433-7851-
dc.identifier.urihttp://hdl.handle.net/10203/207711-
dc.description.abstractDescribed herein is the development of the B(C6F5)(3)(-)catalyzed hydrosilylation of alpha, beta-unsaturated esters and amides to afford synthetically valuable alpha-silyl carbonyl products. The a-silylation occurs chemoselectively, thus leaving the labile carbonyl groups intact. The reaction features a broad scope of both acyclic and cyclic substrates, and the synthetic utility of the obtained alpha-silyl carbonyl products is also demonstrated. Mechanistic studies revealed two operative steps: fast 1,4-hydrosilylation of conjugated carbonyls and then slow silyl group migration of a silyl ether intermediate-
dc.languageEnglish-
dc.publisherWILEY-V C H VERLAG GMBH-
dc.subjectSI BOND FORMATION-
dc.subjectB(C6F5)(3)-CATALYZED HYDROSILYLATION-
dc.subjectKETENE ACETALS-
dc.subjectMETHYL-GROUP-
dc.subjectH-H-
dc.subjectHYDROSILATION-
dc.subjectMECHANISM-
dc.subjectCOMPLEX-
dc.subjectSILICON-
dc.subjectALKENES-
dc.titleBorane-Catalyzed Reductive alpha-Silylation of Conjugated Esters and Amides Leaving Carbonyl Groups Intact-
dc.typeArticle-
dc.identifier.wosid000368065300022-
dc.identifier.scopusid2-s2.0-84955195187-
dc.type.rimsART-
dc.citation.volume55-
dc.citation.issue1-
dc.citation.beginningpage218-
dc.citation.endingpage222-
dc.citation.publicationnameANGEWANDTE CHEMIE-INTERNATIONAL EDITION-
dc.identifier.doi10.1002/anie.201508669-
dc.contributor.localauthorChang, Sukbok-
dc.type.journalArticleArticle-
dc.subject.keywordAuthorboron-
dc.subject.keywordAuthorchemoselectivity-
dc.subject.keywordAuthorconjugation-
dc.subject.keywordAuthorhydrosilylation-
dc.subject.keywordAuthorreaction mechanisms-
dc.subject.keywordPlusSI BOND FORMATION-
dc.subject.keywordPlusB(C6F5)(3)-CATALYZED HYDROSILYLATION-
dc.subject.keywordPlusKETENE ACETALS-
dc.subject.keywordPlusMETHYL-GROUP-
dc.subject.keywordPlusH-H-
dc.subject.keywordPlusHYDROSILATION-
dc.subject.keywordPlusMECHANISM-
dc.subject.keywordPlusCOMPLEX-
dc.subject.keywordPlusSILICON-
dc.subject.keywordPlusALKENES-
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