Reagent-controlled enantioselectivity switch for the asymmetric fluorination of β-ketocarbonyls by chiral primary amine catalysis† †Electronic supplementary information (ESI) available: Experimental details including characterization date, copies of 1H, 13C, and 19F NMR and HPLC traces. See DOI: 10.1039/c6sc03109a Click here for additional data file.
نویسندگان
چکیده
A reagent-controlled enantioselectivity switch was uncovered in the asymmetric a-fluorination of bketocarbonyls by a chiral primary amine catalyst. By a simple swap of fluorination reagents, both enantiomers of the quaternary fluorination adducts could be obtained with good yields and high enantioselectivity. Mechanistic studies disclosed dual H-bonding and electrostatic stereocontrolling modes for the catalysis.
منابع مشابه
Reagent-controlled enantioselectivity switch for the asymmetric fluorination of β-ketocarbonyls by chiral primary amine catalysis.
A reagent-controlled enantioselectivity switch was uncovered in the asymmetric α-fluorination of β-ketocarbonyls by a chiral primary amine catalyst. By a simple swap of fluorination reagents, both enantiomers of the quaternary fluorination adducts could be obtained with good yields and high enantioselectivity. Mechanistic studies disclosed dual H-bonding and electrostatic stereocontrolling mode...
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Department of Organic Chemistry II, Unive P.O. Box 644, 48080 Bilbao, Spain Departamento de Śıntesis y Estructura de Bi y Catálisis Homogénea (ISQCH), Universida Servicio de Resonancia Magnética Nuclear, C (CEQMA), Universidad de Zaragoza, CSIC, † Electronic supplementary information procedures and characterization of all NMR spectra and HPLC chromatogram Cartesian coordinates of all stationary...
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