7306-29-8

Upstream product

• 169477-89-8 4-(3,4-dimethoxyphenyl)-3-methyl-3-buten-2-one 
• 7461-04-3 (R)-1,4-bis-(3,4-dimethoxy-phenyl)-2,3-dimethyl-but-1-ene 
• 120-14-9 3,4-dimethoxy-benzaldehyde 
• 7306-32-3 (R)-3-(3,4-dimethoxyphenyl)-2-methylpropanoic acid 
• 7306-32-3 (S)-3-(3,4-dimethoxyphenyl)-2-methylpropanoic acid 

Relevant academic research and scientific papers

Bioreduction of α-Acetoxymethyl Enones: Proposal for an SN2′ Mechanism Catalyzed by Enereductase

(Z)-3-Acetoxymethyl-4-R-3-buten-2-ones (R=aryl, alkyl) and (Z)-3-methyl-4-R-3-buten-2-ones (R=aryl) were synthesized and submitted to reduction by the yeast Saccharomyces cerevisiae producing the (R)- and (S)-4-R-3-methybutan-2-ones, respectively. This stereochemistry control strategy was applied in the syntheses of (R)- and (S)-Tropional with moderate to high enantiomeric excesses. Other (Z)-3-acyloxymethyl-4-phenyl-3-buten-2-ones showed similar behavior to the (Z)-3-acetoxymethyl counterpart, and the acylated Morita–Baylis–Hillman adduct 1-acetoxy-2-methylene-1-phenylbutan-3-one produced a mixture of products, with and without the acetoxy group, via three different reaction pathways. In addition to experiments employing whole cells, those in which isolated enereductases were used suggested that the main pathway through which the loss of the acetoxy group occurs during the biocatalytic cascade is an SN2′-type reaction, rather than formal hydrogen addition followed by acetic acid elimination. Finally, related ethyl enones were reduced enantioselectively by the yeast Candida albicans, producing both (R)- and (S)-reduction products, depending on the presence of the acetoxy group in the starting material. (Figure presented.).

Stereochemical control in microbial reduction. XXVIII. Asymmetric reduction of α,β-unsaturated ketones with Bakers' yeast

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

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.