169477-89-8Relevant academic research and scientific papers
Stereochemical control in microbial reduction. XXVIII. Asymmetric reduction of α,β-unsaturated ketones with Bakers' yeast
Kawai, Yasushi,Saitou, Kentarou,Hida, Kouichi,Dao, Duc Hai,Ohno, Atsuyoshi
, p. 2633 - 2638 (1996)
Bakers' yeast reduction of α,β-unsaturated ketones affords optically active saturated ketones contaminated by allylic and saturated alcohols as minor components. Stereoselectivity of the reduction of carbon-carbon double bond strongly depends on the structure of β-aryl substituent. The bakers' yeast reduction of β-phenyl enones gives saturated ketones in moderate stereoselectivity. Stereoselectivity is not altered by substitution at the para-position, whereas introduction of a substituent at the ortho- or meta-position drastically improves the stereoselectivity. Deuterium-labeling experiments reveal that the enzymatic reduction of carbon-carbon double bond proceeds with formal trans-addition of hydrogens regardless the efficiency of stereoselectivity. The resulting optically active ketone was converted to the precursor of (S)-iopanoic acid, an inhibitor of thyroxine 5′-deiodinase that is a thyroid hormone-converting enzyme and an oral cholecystographic agent.
Asymmetric Reduction of α,β-Unsaturated Ketones with Bakers' Yeast
Kawai, Yasushi,Saitou, Kentarou,Hida, Kouichi,Ohno, Atsuyoshi
, p. 2143 - 2144 (2007/10/03)
Bakers' yeast reduction of 3-methyl-4-phenyl-3-buten-2-one affords the corresponding saturated (3S)-ketone selectively, while 4-(2-furyl)-3-methyl-3-buten-2-one is selectively transformed to the corresponding (2S)-allylic alcohol.
