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Biotransformations with baker's yeast: pH effects on diastereoselectivity during α-hydroxy-β-ketoester reductions and carboncarbon bond cleavages

Authors
Journal
Tetrahedron Asymmetry
0957-4166
Publisher
Elsevier
Publication Date
Volume
8
Issue
14
Identifiers
DOI: 10.1016/s0957-4166(97)00232-2

Abstract

Abstract Baker's yeast mediated reduction of α-substituted-β-ketoesters lead to reduction of the carbonyl group with high enantiospecificity and diastereoselectivity at low pH (4.0–5.0, e.e.>99%, d.e.>90%) but cleavage of the CC bond is observed at higher pH (>8.0). Similar carbon-carbon bond cleavages are observed in the reactions of α-acetamido-β-ketoesters and acetamidocinnamic acid.

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