183003-17-0

Upstream product

• 100-52-7 benzaldehyde 
• 76154-00-2 diethyl ester of benzylethylmalonic acid 
• 56640-46-1 1-(phenylmethyl)butanoic acid 
• 69390-24-5 3-ethyl-4-phenyl-but-3-en-2-one 
• 917-54-4 methyllithium 
• 58635-83-9 (S)-2-(phenylmethyl)butyric acid 
• 107-87-9 2-Pentanone 
• 69390-24-5 (E)-3-ethyl-4-phenyl-3-buten-2-one 

Relevant academic research and scientific papers

Extractive biocatalysis in the asymmetric reduction of α-alkyl, β-aryl enones by Baker's yeast

We prepared various chiral α-alkyl, β-aryl ketones with good to excellent enantiomeric excess through the Baker's yeast asymmetric double-bond reduction of the corresponding α,β-unsaturated substrates adsorbed onto the resin Amberlite XAD-7. This methodology was compatible with substrates bearing both electron-donating and withdrawing groups attached to the aromatic ring. Elongation of the α-alkyl substituent of the starting material strongly affected the reactivity and enantioselectivity of the reaction.

Substrate scope and synthetic applications of the enantioselective reduction of α-alkyl-β-arylenones mediated by Old Yellow Enzymes

The ene-reductases mediated bioreduction of a selection of open-chain α-alkyl-β-aryl enones afforded the corresponding saturated α-chiral ketones in high yield and optical purity in several cases. The stereo-electronic requirements of the reaction have been investigated, considering the nature and location of substituents on the aromatic ring as well as the steric hindrance at the α-position and adjacent to the carbonyl functionality. The general considerations drawn allow us to guide the design of α,β-unsaturated ketones to be employed as substrates of ene-reductases in future preparative applications. An interesting case of orthogonality between enzyme-based and substrate-based stereocontrol within the highly homologous ene-reductases from Saccharomyces species (OYE1-3) has been reported and rationalized with the help of computational docking studies. Furthermore, to demonstrate the synthetic versatility of the reaction, the key chiral precursors of biologically active compounds such as (2′R)- stenusines and (S)-iopanoic acid were obtained. The very robust protocol allowed us to run the reactions on preparative scale in quantitative yields, with a simple work-up and no chromatographic purification steps. The Royal Society of Chemistry 2013.

Development of catalysts for the stereoselective hydrogenation of α,β-unsaturated ketones

Iridium phosphinitoxazoline complexes were found to be new efficient catalysts for the asymmetric hydrogenation of arylated α,β- unsaturated ketones. Linear as well as cyclic substrates are hydrogenated with similar success, giving selectivities of up to 99.7% ee.

Highly enantioselective synthesis of optically active ketones by iridium-catalyzed asymmetric hydrogenation

(Chemical Equation Presented) Close to perfect enantioselectivity (up to 99% ee, see scheme) is found for the formation of α-substituted ketones by the asymmetric hydrogenation of enones with an iridium-phosphinooxazoline catalyst. In an operationally simple process, both linear and cyclic substrates react well and afford the desired products in high yields. A wide variety of substituents are tolerated, thus making the method synthetically appealing.

Pyran-2-ones and 5,6-dihydropyran-2-ones useful for treating hyperplasia and other diseases

Certain 2H-pyran-2-ones are useful for treating benign prostatic hypertrophy or hyperplasia, prostatic cancer, alopecia, hirsutism, acne vulgaris and seborrhea.

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.