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Enantiopure Triazolium Salts: Chemoenzymatic Synthesis and Applications in Organocatalysis

dc.contributor.authorRíos Lombardía, Nicolás 
dc.contributor.authorPorcar García, Raúl
dc.contributor.authorBusto García, Benjamín Eduardo 
dc.contributor.authorAlfonso Rodríguez, Ignacio 
dc.contributor.authorMontejo Bernardo, José Manuel 
dc.contributor.authorGarcía-Granda, Santiago 
dc.contributor.authorGotor Santamaría, Vicente Miguel 
dc.contributor.authorLuis Lafuente, Santiago Vicente
dc.contributor.authorGarcía Verdugo, Eduardo
dc.contributor.authorGotor Fernández, Vicente 
dc.date.accessioned2013-01-30T10:08:08Z
dc.date.available2013-01-30T10:08:08Z
dc.date.issued2011
dc.identifier.citationChemoenzymatic Synthesis and Applications in Organocatalysis. ChemCatChem, 3(12), p. 1921–1928 (2011); doi:10.1002/cctc.201100218spa
dc.identifier.issn1867-3899
dc.identifier.urihttp://hdl.handle.net/10651/8463
dc.description.abstractA novel family of triazolium salt enantiomers has been efficiently synthesized by combining chemical and biocatalytic methods. The stereoselective action shown by hydrolytic enzymes led to the design of simple and general chemoenzymatic routes in which tunable vectors, such as ring size, substituent stereochemistry, oxygen substitution, anion nature, or N4-triazole alkylating chain, were considered to produce 30 enantiopure triazolium salts in very high overall yields. Finally, selected triazolium salts were tested as phase-transfer catalysts in the asymmetric Michael addition of diethyl malonate to trans-chalcone to rationalize their activity and stereopreference. Low to complete conversion values were achieved in the formation of the Michael addition adduct, which mainly gave low levels of stereoselectivity depending on the different structural patterns considered in this systematic study.spa
dc.description.sponsorshipMinisterio de Ciencia e Innovación. Grant Numbers: MICINN CTQ2007-61126, CTQ2008-04412, CTQ2008-04309, CTQ2009-14366-C02. UJI-BANCAIXA. Grant Number: P1-1A2009-58. MICINN. FICYT.
dc.language.isoeng
dc.relation.ispartofChemCatChemspa
dc.rights(c) WILEY-VCH Verlag GmbH & Co.
dc.sourceWILEYspa
dc.subjectAsymmetric Synthesis; Biocatalysis; Chirality; Organocatalysis; Triazolespa
dc.titleEnantiopure Triazolium Salts: Chemoenzymatic Synthesis and Applications in Organocatalysisspa
dc.typejournal article
dc.identifier.local20110753spa
dc.identifier.doi10.1002/cctc.201100218
dc.relation.projectIDMICINN/CTQ2007-61126
dc.relation.projectIDMICINN/CTQ2008-04412
dc.relation.projectIDMICINN/CTQ2008-04309
dc.relation.projectIDMICINN/CTQ2009-14366-C02
dc.relation.publisherversionhttp://dx.doi.org/10.1002/cctc.201100218spa


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