Chemo- and stereoselective reduction of an alpha-cyanoketone by bakers' yeast at low temperature

Authors
Florey, P Smallridge, AJ Ten, A Trewhella, MA
Citation
P. Florey et al., Chemo- and stereoselective reduction of an alpha-cyanoketone by bakers' yeast at low temperature, ORG LETT, 1(12), 1999, pp. 1879-1880
Citations number
5
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
ORGANIC LETTERS
ISSN journal
15237060 → ACNP
Volume
1
Issue
12
Year of publication
1999
Pages
1879 - 1880
Database
ISI
SICI code
1523-7060(199912)1:12<1879:CASROA>2.0.ZU;2-O
Abstract
[GRAPHICS] The bakers' yeast mediated reduction of 3-oxo-3-phenylpropanenitrile (1) pr oceeds at 4 degrees C to give exclusive ly (S)-3-hydroxy-3-phenylpropanenit rile (3) in 59% yield. This is in contrast to the corresponding reaction at room temperature which yields a mixture of reduction and alkylation produc ts. This work demonstrates the use of low temperature to improve yeast sele ctivity.