Preparative Biorganic Chemistry Part 10 Asymmetric Reduction of Bicyclo[2.2.2]Octane-2,6-Diones with Baker's Yeast
- 1 January 1990
- journal article
- research article
- Published by Taylor & Francis in Biocatalysis
- Vol. 3 (1-2) , 25-36
- https://doi.org/10.3109/10242429008992046
Abstract
Reduction of bicyclo[2.2.2]octane-2,6-dione with baker's yeast gave (lR,4S,6S)-6-hydroxybi-cyclo[2.2.2]octan-2-one (95% e.e.) contaminated with 8% of its (1S,4R,6S)-isomer. Similarly, the yeast reduction of 1-methylbicyclo[2.2.2]octane-2,6-dione furnished (1R,4S,6S)-6-hydroxy-1-methylbi-cyclo[2.2.2.]octan-2-one (99.5% e.e.) in 59% yield. The yeast reduction of 4-methylbi-cyclo[2.2.2.]octane-2,6-dione afforded (1R,4S,6S)-6-hydroxy-4-methylbicyclo[2.2.2.]octan-2-one (98% e.e.) contaminated with 3% of its (1S,4R,6S)-isomer in 58% yield.Keywords
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