Enantioselective Synthesis of 4-(Dimethylamino)pyridinesthrough a Chemical Oxidation-Enzymatic Reduction Sequence.Application in Asymmetric Catalysis
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Enantiomerically pure 4-(dimethylamino)-3-(1-hydroxyalkyl)pyridines and 4-(dimethylamino)-3-[hydroxyACHTUNGTRENNUNG(phenyl)methyl]pyridine have been pre-pared through efficient chemoenzymatic routes. Forthis purpose different lipases and oxidoreductaseshave been tested in the preparation of opticallyactive 4-chloro derivatives and baker´s yeast wasfound to be an excellent catalyst for the bioreduc-tions of the corresponding ketones. Their applica-tions as enantioselective nucleophilic catalysts havebeen studied, important catalytic properties were ob-served in the stereoselective construction of quater-nary centers
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We thank Novo Nordisk Co. for the generous gift of theCAL-B (Novozyme 435) and Jlich Fine Chemicals for alco-hol dehydrogenases from Thermoanaerobacter species (T-ADH) and Lactobacillus brevis (LB-ADH). Financial sup-port of this work by the European Project EU-04-LSHB-2003–503017 is gratefully acknowledged. V.G.-F. thanksMEC for a personal grant (Juan de la Cierva Program). E.B.thanks MEC for a pre-doctoral fellowship
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