Mo, Kilwoong Kang, Soon Bang Kim, Youseung Lee, Yong Sup Lee, Jae Wook Keum, Gyochang 2024-01-20T08:00:37Z 2024-01-20T08:00:37Z 2021-09-04 2015-02 1434-193X https://pubs.kist.re.kr/handle/201004/125828 The baker's yeast mediated reduction of beta-keto-alpha-oximino nitriles 3 at 20 degrees C gave beta-hydroxy-alpha-oximino nitriles 4 in high yields with high enantiomeric purity [enantiomeric excess (ee) values >99%]. At room temperature, the same reaction afforded the product in a slightly lower yield. The beta-hydroxy-alpha-oximino nitriles 4 were obtained as single stereoisomers according to chiral GC-MS analyses and the H-1 and F-19 NMR spectra of the corresponding Mosher esters. The absolute stereochemistry of alcohol 4a was determined by hydrolysis of its oximino nitrile group followed by conversion into its corresponding alpha-hydroxy ester. The beta-hydroxy-alpha-oximino nitrile products were further submitted to oxime-and nitrile-selective transformations. This chemo- and stereoselective reduction can be used to generate important chiral building blocks. English WILEY-V C H VERLAG GMBH ASYMMETRIC TRANSFER HYDROGENATION ABSOLUTE-CONFIGURATION BIOCATALYTIC REDUCTION COFACTOR REGENERATION PRACTICAL SYNTHESIS CARBONYL REDUCTASE HYDROXY TRANSFORMATION ALKYLATION FLUOXETINE Chemo- and Stereoselective Reduction of beta-Keto-alpha-oximino Nitriles by Using Baker's Yeast Article 10.1002/ejoc.201403393 1 EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, v.2015, no.5, pp.1137 - 1143 EUROPEAN JOURNAL OF ORGANIC CHEMISTRY 2015 5 1137 1143 scie scopus 000349391700027 2-s2.0-84922311735 Chemistry, Organic Chemistry Article ASYMMETRIC TRANSFER HYDROGENATION ABSOLUTE-CONFIGURATION BIOCATALYTIC REDUCTION COFACTOR REGENERATION PRACTICAL SYNTHESIS CARBONYL REDUCTASE HYDROXY TRANSFORMATION ALKYLATION FLUOXETINE Synthetic methods Biotransformations Reduction Chemoselectivity Enantioselectivity