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Synthesis 1986; 1986(1): 37-40
DOI: 10.1055/s-1986-31468
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(R)-Ethyl 4-t-Butoxy-3-hydroxybutanoate, a Versatile Chiral Building Block for EPC (Enantiomerically Pure Compound) Syntheses, by Yeast Reduction of Ethyl 4-t-Butoxy-3-oxobutanoate

Dieter Seebach* , Martin Eberle
  • *Laboratorium für organische Chemie der Eidgenössischen Technischen Hochschule, ETH-Zentrum, Universitätstr. 16, CH-8092 Zürich, Switzerland
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Publication Date:
20 August 2002 (online)

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Reduction of ethyl 4-t-butoxy-3-oxobutanoate with fermenting yeast yields (R)-ethyl 4-t-butoxy-3-hydroxybutanoate in 97% e.e. Since the protective group is readily removed from the product of reduction, the present procedure provides a simple entry to the "world of chiral blocks" formally derived from (R)-malic acid.