Baker's yeast mediated reduction of β-keto esters and β-keto amides in an organic solvent system |
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Authors: | Nick Athanasiou Andrew J Smallridge Maurie A Trewhella |
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Affiliation: | Biocatalytic Synthesis Unit, School of Life Sciences and Technology (F008), Victoria University of Technology, PO Box 14428, Melbourne, MC 8001,Victoria, Australia |
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Abstract: | The baker's yeast mediated reduction of four β-keto esters in petroleum ether indicated that the size of the group attached to the keto carbon affected their reactivity. Ethyl 3-phenyl-3-oxopropanoate (1), which has a phenyl group directly attached to the keto carbon, is incompletely reduced using 20 g yeast/mmol substrate, ethyl 4-phenyl-3-oxobutanoate (2), which has one methylene group between the phenyl and keto carbon, was also incompletely reduced using 20 g yeast/mmol, although the extent of reduction was about double that of (1), ethyl 5-phenyl-3-oxopentanoate (3), which has two methylene groups between the phenyl and keto carbon, is completely reduced using 10 g yeast/mmol and ethyl 3-oxobutanoate (4), which has a methyl group attached to the keto carbon shows complete reduction using only 1 g yeast/mmol. The corresponding β-keto amides are considerably less reactive than the corresponding β-keto esters with only the amides derived from ethyl 3-oxobutanoate indicating any significant reduction using 20 g yeast/mmol. |
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Keywords: | Baker's yeast β-Keto esters Organic solvent system |
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