title: Chemo- and stereoselective reduction of an alpha-cyanoketone by bakers' yeast at low temperature.
abstract: [formula: see text] The bakers' yeast mediated reduction of 3-oxo-3-phenylpropanenitrile (1) proceeds at 4 degrees C to give exclusively (S)-3-hydroxy-3-phenylpropanenitrile (3) in 59% yield. This is in contrast to the corresponding reaction at room temperature which yields a mixture of reduction and alkylation products. This work demonstrates the use of low temperature to improve yeast selectivity.
authors.affiliation: School of Life Sciences and Technology, Victoria University of Technology, Melbourne City, Australia.
authors.forename: P
authors.initials: P
authors.lastname: Florey
authors.forename: A J
authors.initials: AJ
authors.lastname: Smallridge
authors.forename: A
authors.initials: A
authors.lastname: Ten
authors.forename: M A
authors.initials: MA
authors.lastname: Trewhella
mesh_terms: D000478:Alkylation; D009570:Nitriles / Q000737:chemistry*; D010084:Oxidation-Reduction; D012441:Saccharomyces cerevisiae / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D009570:Nitriles; C410426:3-oxo-3-phenylpropanenitrile