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Please use this identifier to cite or link to this item: http://hdl.handle.net/10651/8463

Title: Enantiopure Triazolium Salts: Chemoenzymatic Synthesis and Applications in Organocatalysis
Author(s): Ríos Lombardía, Nicolás
Porcar García, Raúl
Busto García, Benjamín Eduardo
Alfonso Rodríguez, Ignacio
Montejo Bernardo, José Manuel
García-Granda, Santiago
Gotor Santamaría, Vicente Miguel
Luis Lafuente, Santiago Vicente
García Verdugo, Eduardo
Gotor Fernández, Vicente
Keywords: Asymmetric Synthesis; Biocatalysis; Chirality; Organocatalysis; Triazole
Issue date: 2011
Publisher version: http://dx.doi.org/10.1002/cctc.201100218
Citation: Chemoenzymatic Synthesis and Applications in Organocatalysis. ChemCatChem, 3(12), p. 1921–1928 (2011); doi:10.1002/cctc.201100218
Abstract: A 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.
URI: http://hdl.handle.net/10651/8463
ISSN: 1867-3899
Local identifier: 20110753
Sponsored: Ministerio 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.
Project id.: MICINN/CTQ2007-61126
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