Chemo- and Stereoselective Reduction of an α-Cyanoketone by Bakers' Yeast at Low Temperature

Chemo- and Stereoselective Reduction of an α-Cyanoketone by Bakers' Yeast at Low Temperature

The bakers' yeast mediated reduction of 3-oxo-3-phenylpropanenitrile (1) proceeds at 4 °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....

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Veröffentlicht in:Organic letters 1999-12, Vol.1 (12), p.1879-1880
Hauptverfasser: Florey, Peter, Smallridge, Andrew J, Ten, Abilio, Trewhella, Maurie A
Format: Artikel
Sprache:eng
Schlagworte:
Alkylation
Nitriles - chemistry
Oxidation-Reduction
Saccharomyces cerevisiae - chemistry
Stereoisomerism
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Zusammenfassung:The bakers' yeast mediated reduction of 3-oxo-3-phenylpropanenitrile (1) proceeds at 4 °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.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol990833y