2,2 '-Dihydroxybenzil: A Stereodynamic Probe for Primary Amines Controlled by Steric Strain

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dc.contributor.authorSeo, Min Seobko
dc.contributor.authorLee, An Sooko
dc.contributor.authorKim, Hyunwooko
dc.date.accessioned2014-12-16-
dc.date.available2014-12-16-
dc.date.created2014-07-07-
dc.date.created2014-07-07-
dc.date.issued2014-06-
dc.identifier.citationORGANIC LETTERS, v.16, no.11, pp.2950 - 2953-
dc.identifier.issn1523-7060-
dc.identifier.urihttp://hdl.handle.net/10203/192705-
dc.description.abstractA rational approach for generating 1,1'-binaphthalene-like axial chirality of a small organic receptor, 2,2'-dihydroxybenzil is presented. The receptor combines with 2 equiv of monodentate primary amines to form a diimine, of which axial chirality is controlled by steric strain with moderate (1.4:1) to good (4.7:1) stereoselectivity. The observed circular dichroism (CD) spectra have been closely simulated by TD-DFT computations and can be used for determining the absolute chirality and enantiomeric excess of primary amines.-
dc.languageEnglish-
dc.publisherAMER CHEMICAL SOC-
dc.subjectCHIRAL CARBOXYLIC-ACIDS-
dc.subjectABSOLUTE-CONFIGURATION DETERMINATION-
dc.subjectCIRCULAR-DICHROISM SPECTROSCOPY-
dc.subjectDIAZA-COPE REARRANGEMENT-
dc.subjectINDUCED AXIAL CHIRALITY-
dc.subjectENANTIOMERIC EXCESS-
dc.subjectSUPRAMOLECULAR CHIROGENESIS-
dc.subjectRAPID-DETERMINATION-
dc.subjectSECONDARY ALCOHOLS-
dc.subjectGUEST STRUCTURE-
dc.title2,2 '-Dihydroxybenzil: A Stereodynamic Probe for Primary Amines Controlled by Steric Strain-
dc.typeArticle-
dc.identifier.wosid000337074300043-
dc.identifier.scopusid2-s2.0-84902083809-
dc.type.rimsART-
dc.citation.volume16-
dc.citation.issue11-
dc.citation.beginningpage2950-
dc.citation.endingpage2953-
dc.citation.publicationnameORGANIC LETTERS-
dc.identifier.doi10.1021/ol501088v-
dc.embargo.liftdate9999-12-31-
dc.embargo.terms9999-12-31-
dc.contributor.localauthorKim, Hyunwoo-
dc.type.journalArticleArticle-
dc.subject.keywordPlusCHIRAL CARBOXYLIC-ACIDS-
dc.subject.keywordPlusABSOLUTE-CONFIGURATION DETERMINATION-
dc.subject.keywordPlusCIRCULAR-DICHROISM SPECTROSCOPY-
dc.subject.keywordPlusDIAZA-COPE REARRANGEMENT-
dc.subject.keywordPlusINDUCED AXIAL CHIRALITY-
dc.subject.keywordPlusENANTIOMERIC EXCESS-
dc.subject.keywordPlusSUPRAMOLECULAR CHIROGENESIS-
dc.subject.keywordPlusRAPID-DETERMINATION-
dc.subject.keywordPlusSECONDARY ALCOHOLS-
dc.subject.keywordPlusGUEST STRUCTURE-
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