75391-06-9

Upstream product

• 123-11-5 4-methoxy-benzaldehyde 
• 96-22-0 pentan-3-one 
• 52750-05-7 ethyl (E)-3-(4-methoxyphenyl)-2-methylpropenoate 

Downstream Products

• 1326755-37-6 (2S)-1-(4-methoxyphenyl)-2-methyl-3-pentanone 

Relevant academic research and scientific papers

Nazarov cyclization of divinyl ketones bearing an ester group at the β-position: A remarkable effect of α-substitution and alkene geometry on regioselectivity

The Nazarov cyclization of divinyl ketones with an ester at the β-position was examined with particular reference to where the cyclic double bond forms. We observed unprecedented regioselectivity, dictated by the subtle substitution patterns at the α-position and alkene geometry of α,β and mostly, this selectivity is regardless of substitutions at α′- and β′-positions. The major implications of these observations are an aromatic group at the α-position with E-olefin geometry provides a cyclopentenone in which the double bond is not in conjugation with an ester, whereas Z-olefin provides a cyclopentenone in which the double bond is in conjugation with an ester; and divinyl ketones bearing an ester group at the β-position and an alkyl group at the α-position with E-olefin geometry provide a cyclopentenone in which the double bond is in conjugation with the ester.

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.

Lithium Iodide-promoted Aldol Condensation Reactions

Anhydrous lithium iodide in ether, tetrahydrofuran, or benzene is an effective reagent for the formation of α,β-unsaturated ketones by condensation of alkyl ketones with enolisable and non-enolisable aldehydes; in the presence of trimethylchlorosilane-triethylamine enone formation is suppressed and high yields of 1,3-hydroxyketones are obtained as their trimethylsilyl ether derivatives.