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College of Natural Sciences(자연과학대학)Dept. of Chemistry(화학과)CH-Journal Papers(저널논문)

Intramolecular, reductive cyclization of beta-ketoisothiocyanates promoted by using samarium diiodide

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dc.contributor.authorCho, MSko
dc.contributor.authorLee, ISko
dc.contributor.authorKang, SungHoko
dc.contributor.authorKim, Yong Haeko
dc.date.accessioned2013-03-07T08:25:15Z-
dc.date.available2013-03-07T08:25:15Z-
dc.date.created2012-02-06-
dc.date.created2012-02-06-
dc.date.issued2005-02-
dc.identifier.citationCHEMISTRY-A EUROPEAN JOURNAL, v.11, no.5, pp.1452 - 1458-
dc.identifier.issn0947-6539-
dc.identifier.urihttp://hdl.handle.net/10203/89786-
dc.description.abstractA novel samarium diiodide (SmI2) promoted intramolecular cyclization of beta-ketoisothiocyanate, derived from alpha,beta-unsaturated esters and ammonium thiocyanate led to alpha-hydroxythiolactams and/or thiolactams in high yields. Treatment of beta-ketoisothiocyanate with two equivalents of SmI2 gave a mixture of alpha-hydroxythiolactam and thiolactam. Four equivalents of SmI2 afforded only thiolactam in high yields. The intramolecular cyclization took place with high to complete stereoselectivity. A mechanism to explain this transformation is proposed.-
dc.languageEnglish-
dc.publisherWILEY-V C H VERLAG GMBH-
dc.subjectORGANIC-SYNTHESIS-
dc.subjectCOUPLING REACTIONS-
dc.subjectCARBONYL-COMPOUNDS-
dc.subjectORGANOPHOSPHORUS COMPOUNDS-
dc.subjectIODIDE-
dc.subjectSMI2-
dc.subjectTHIOLACTAMS-
dc.subjectLANTHANIDES-
dc.subjectCONVERSION-
dc.subjectESTERS-
dc.titleIntramolecular, reductive cyclization of beta-ketoisothiocyanates promoted by using samarium diiodide-
dc.typeArticle-
dc.identifier.wosid000227262000009-
dc.identifier.scopusid2-s2.0-14844309384-
dc.type.rimsART-
dc.citation.volume11-
dc.citation.issue5-
dc.citation.beginningpage1452-
dc.citation.endingpage1458-
dc.citation.publicationnameCHEMISTRY-A EUROPEAN JOURNAL-
dc.identifier.doi10.1002/chem.200400676-
dc.contributor.localauthorKang, SungHo-
dc.contributor.nonIdAuthorCho, MS-
dc.contributor.nonIdAuthorLee, IS-
dc.type.journalArticleArticle-
dc.subject.keywordAuthorcyclization-
dc.subject.keywordAuthordiastereoselectivity-
dc.subject.keywordAuthorheterocycles-
dc.subject.keywordAuthorradical reactions-
dc.subject.keywordAuthorsamarium-
dc.subject.keywordPlusORGANIC-SYNTHESIS-
dc.subject.keywordPlusCOUPLING REACTIONS-
dc.subject.keywordPlusCARBONYL-COMPOUNDS-
dc.subject.keywordPlusORGANOPHOSPHORUS COMPOUNDS-
dc.subject.keywordPlusIODIDE-
dc.subject.keywordPlusSMI2-
dc.subject.keywordPlusTHIOLACTAMS-
dc.subject.keywordPlusLANTHANIDES-
dc.subject.keywordPlusCONVERSION-
dc.subject.keywordPlusESTERS-
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CH-Journal Papers(저널논문)
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