143191-63-3

Upstream product

• 58889-89-7 (Z)-1-methoxy-1-(4-methoxyphenyl)-1-propene 
• 200353-84-0 1-(4-methoxyphenyl)-1-oxopropan-2-yl acetate 
• 10557-27-4 1-(4-methoxy-phenyl)-propane-1,2-dione 
• 123-11-5 4-methoxy-benzaldehyde 
• 75-07-0 acetaldehyde 
• 121-97-1 4-Methoxypropiophenone 
• 530085-88-2 phosphoric acid diethyl ester 1-(4-methoxyphenyl)-propenyl ester 
• 143215-10-5 (Z)-1-(4-methoxyphenyl)-1-(tert-butyldimethylsiloxy)-1-propene 

Relevant academic research and scientific papers

α-Hydroxy Ketones in High Enantiomeric Purity from Asymmetric Dihydroxylation of Enol Ethers

Highly enantioselective construction of α-hydroxy ketones by the osmium-catalyzed asymmetric dihydroxylation of the corresponding enol ethers has been achieved.

Synthesis and Rhizopus oryzae mediated enantioselective hydrolysis of α-acetoxy aryl alkyl ketones

Mn(OAc)3 oxidation of aromatic ketones afforded the α-acetoxy ketones in good yield. Selective hydrolysis of the acetoxy ketones by the fungus Rhizopus oryzae yields (R)-hydroxy ketones in high enantiomeric excess.

Biocatalytic route to chiral acyloins: P450-catalyzed regio- and enantioselective α-hydroxylation of ketones

P450-BM3 and mutants of this monooxygenase generated by directed evolution are excellent catalysts for the oxidative α-hydroxylation of ketones with formation of chiral acyloins with high regioselectivity (up to 99%) and enantioselectivity (up to 99% ee). This constitutes a new route to a class of chiral compounds that are useful intermediates in the synthesis of many kinds of biologically active compounds.

Asymmetric oxidation of enol phosphates to α-hydroxy ketones using Sharpless reagents and a fructose derived dioxirane

The asymmetric oxidation of a variety of differently substituted, acyclic and cyclic enol phosphates using the Sharpless AD-reagents AD-mix-α and AD-mix-β, and a fructose derived chiral ketone as a catalyst, afforded the corresponding α-hydroxy ketones in high enantioselectivity and good yield. The influence of steric and electronic factors of the substrates on the facial stereoselectivity in the reported oxidations was studied.

Studies towards the stereoselective α-hydroxylation of flavanones. Biosynthetic significance

The enolates of various propiophenones, chromanones, and also analogues of naturally occurring flavanones were stereoselectively hydroxylated at the ?-position, by employing commercially available enantiopure oxaziridines, to afford the desired ?-hydroxylated target molecules in good to exceptional stereoselectivities and in moderate to good chemical yields. A mechanistic rationale is presented to account for the stereoselectivities achieved. These in vitro results were tentatively related to the stereoselective biosynthesis of enantio-enriched dihydroflavonols while questions were raised about the authenticity of certain natural compounds. CSIRO 2008.

Asymmetric oxidation of enol phosphates to α-hydroxy ketones by?(salen)manganese(III) complex. Effects of the substitution pattern of enol phosphates on the stereochemistry of oxygen?transfer

This paper presents a study of enantioselective catalytic oxidation of a variety of differently substituted, cyclic (E) and acyclic (Z)-enol phosphates. The asymmetric oxidation of acyclic (Z)-enol phosphates containing alkoxy substituents in the phosphate group 2a, c, e-g, i, and j and Z-configured enol phosphates containing aryloxy substituents in the phosphate group 2b, d, and h afforded optically active α-hydroxy ketones 4a-j of opposite configuration with good to high enantioselectivity. The influence of electronic and steric effects of the enol phosphate substituents on the stereoselectivity of oxidation was studied.

α-Hydroxy ketones in high enantiomeric purity from asymmetric oxidation of enol phosphates with (salen) manganese(III) complex

Optically active α-hydroxy ketones 4 have been prepared in high enantioselectivity by the catalytic, enantioselective oxidation of easily available and stable (E)-enol phosphates 2 by (salen) Mn(III) complex.

Enantioselective Synthesis of α-Hydroxy Ketones via Benzaldehyde Lyase-Catalyzed C-C Bond Formation Reaction

(R)-Benzoins and (R)-2-hydroxypropiophenone derivatives are formed on a preparative scale by benzaldehyde lyase (BAL)-catalyzed C-C bond formation from aromatic aldehydes and acetaldehyde in aqueous buffer/ DMSO solution with remarkable ease in high chemical yield and high optical purity. The substrate range of this thiamin diphosphate-dependent enzyme was examined with respect to a broad applicability of this benzoin condensation-type reaction in stereoselective synthesis.

Stereoselective Synthesis of Optically Active α-hydroxy Ketones and anti-1,2-diols via Asymmetric Transfer Hydrogenation of Unsymmetrically Substituted 1,2-diketones

Formula Represented A well-defined chiral Ru catalyst RuCl(N-(p-toluenesulfonyl)-1,2-diphenylethylenediamine)(η6-arene) effectively promotes asymmetric transfer hydrogenation of 1-aryl-1,2-propanedione with HCOOH/N(C2H5)3, leading preferentially to optically active 1-aryl-2-hydroxy-1-propanone with up to 99% ee and 89% yield at 10°C. The reaction at 40°C gives anti-1-aryl-1,2-propanediol with up to 95% ee and 78% yield. This is a highly efficient procedure for the synthesis of optically active anti-diols.

Benzoylformate decarboxylase from Pseudomonas putida as stable catalyst for the synthesis of chiral 2-hydroxy ketones

The thiamin diphosphate-and Mg2+-dependent enzyme benzoylformate decarboxylase (BFD) from Pseudomonas putida was characterized with respect to its suitability to catalyze the formation of chiral 2-hydroxy ketones in a benzoin-condensation type reaction. Carboligation constitutes a side reaction of BFD, whereas the predominant physiological task of the enzyme is the non-oxidative decarboxylation of benzoylformate. For this purpose the enzyme was obtained in sufficient purity from Pseudomonas putida cells in a one-step purification using anion-exchange chromatography. To facilitate the access to pure BFD for kinetical studies, stability investigations, and synthetical applications, the coding gene was cloned into a vector allowing the expression of a hexahistidine fusion protein. The recombinant enzyme shows distinct activity maxima for the decarboxylation and the carboligation beside a pronounced stability in a broad pH and temperature range. The enzyme accepts a wide range of donor aldehyde substrates which are ligated to acetaldehyde as an acceptor in mostly high optical purities. The enantioselectivity of the carboligation was found to be a function of the reaction temperature, the substitution pattern of the donor aldehyde and, most significantly, of the concentration of the donor aldehyde substrate. Our data are consistent with a mechanistical model based on the X-ray crystallographic data of BFD. Furthermore we present a simple way to increase the enantiomeric excess of (S)-2-hydroxy-1-phenyl-propanone from 90% to 95% by skillful choice of the reaction parameters. Enzymatic synthesis with BFD are performed best in a continuously operated enzyme membrane reactor. Thus, we have established a new enzyme tool comprising a vast applicability for stereoselective synthesis.