Chemo- and stereoselective reduction of an alpha-cyanoketone by bakers' yeast at low temperature.
[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.
Florey
P
P
School of Life Sciences and Technology, Victoria University of Technology, Melbourne City, Australia.
Smallridge
A J
AJ
Ten
A
A
Trewhella
M A
MA
D000478:Alkylation; D009570:Nitriles / Q000737:chemistry*; D010084:Oxidation-Reduction; D012441:Saccharomyces cerevisiae / Q000737:chemistry*; D013237:Stereoisomerism
D009570:Nitriles; C410426:3-oxo-3-phenylpropanenitrile