Chiral imine copper chloride-catalyzed enantioselective desymmetrization of 2-substituted 1,2,3-propanetriols

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dc.contributor.authorJung, Bko
dc.contributor.authorKang, SungHoko
dc.date.accessioned2013-03-07T18:56:51Z-
dc.date.available2013-03-07T18:56:51Z-
dc.date.created2012-02-06-
dc.date.created2012-02-06-
dc.date.issued2007-01-
dc.identifier.citationPROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, v.104, no.5, pp.1471 - 1475-
dc.identifier.issn0027-8424-
dc.identifier.urihttp://hdl.handle.net/10203/90994-
dc.description.abstractCatalytic enantioselective desymmetrization of meso-2-substituted glycerols has been developed to secure a novel synthetic route to chiral tertiary alcohols. The transformation has been realized by monobenzoylation using benzoyl chloride and triethylamine in the presence of the imine ligand (25)-CuCl2 complex in THF at ambient temperature. The desymmetrization turned out to be greatly dependent on acylating reagent, base, solvent, and needless to say, catalyst. Extensive screening of chiral ligands led us to combine bromopyridinecarboxaldehyde 1 and phenyloxazoline amine 12 derived from tert-leucine, the bromo and phenyl substituents of which proved to be indispensable. All of the substrates have been desymmetrized to the corresponding monobenzoates with high enantioselectivity up to 96% enantiomeric excess. The catalytic system allows broad structural diversity of substrates and its synthetic versatility has been demonstrated by an efficient synthetic route to a known key precursor 68 of triazole antifungals.-
dc.languageEnglish-
dc.publisherNATL ACAD SCIENCES-
dc.subjectASYMMETRIC ADDITION-
dc.subjectENZYMATIC ASYMMETRIZATION-
dc.subjectQUATERNARY STEREOCENTERS-
dc.subjectKINETIC RESOLUTION-
dc.subjectALKYLZINC REAGENTS-
dc.subjectALIPHATIC-KETONES-
dc.subjectANTIFUNGAL AGENTS-
dc.subjectKEY INTERMEDIATE-
dc.subjectHIGHLY EFFICIENT-
dc.subjectALDOL ADDITIONS-
dc.titleChiral imine copper chloride-catalyzed enantioselective desymmetrization of 2-substituted 1,2,3-propanetriols-
dc.typeArticle-
dc.identifier.wosid000244081000008-
dc.identifier.scopusid2-s2.0-33846828832-
dc.type.rimsART-
dc.citation.volume104-
dc.citation.issue5-
dc.citation.beginningpage1471-
dc.citation.endingpage1475-
dc.citation.publicationnamePROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA-
dc.identifier.doi10.1073/pnas.0607865104-
dc.contributor.localauthorKang, SungHo-
dc.contributor.nonIdAuthorJung, B-
dc.type.journalArticleArticle-
dc.subject.keywordAuthorbromopyridinecarboxaldehyde-
dc.subject.keywordAuthorchiral tertiary alcohols-
dc.subject.keywordAuthormeso-2-substituted glycerols-
dc.subject.keywordAuthorphenyloxazoline amine-
dc.subject.keywordPlusASYMMETRIC ADDITION-
dc.subject.keywordPlusENZYMATIC ASYMMETRIZATION-
dc.subject.keywordPlusQUATERNARY STEREOCENTERS-
dc.subject.keywordPlusKINETIC RESOLUTION-
dc.subject.keywordPlusALKYLZINC REAGENTS-
dc.subject.keywordPlusALIPHATIC-KETONES-
dc.subject.keywordPlusANTIFUNGAL AGENTS-
dc.subject.keywordPlusKEY INTERMEDIATE-
dc.subject.keywordPlusHIGHLY EFFICIENT-
dc.subject.keywordPlusALDOL ADDITIONS-
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