111197-79-6

Upstream product

• 1855-08-9 1-(p-Tolyl)-1,2-propanedione 
• 5337-93-9 4'-methylpropiophenone 
• 2698-14-8 1-methyl-4-(prop-1-enyl)benzene 
• 104-87-0 4-methyl-benzaldehyde 
• 75-07-0 acetaldehyde 
• 73208-70-5 ethyl (2S)-2-(tetrahydropyran-2-yloxy)propionate 
• 111199-11-2 (S)-2-methoxymethoxy-1-(4-methylphenyl)-1-propanone 

Downstream Products

• 111197-83-2 (S)-2-hydroxy-1-(4-methylphenyl)-1-propanone dimethyl acetal 
• 103593-52-8 (S)-2-methylsulfonyloxy-1-(4-methylphenyl)-1-propanone dimethyl acetal 
• 103593-53-9 (S)-2-methylsulfonyloxy-1-(4-methylphenyl)-1-propanone 2,2-dimethyl-trimethylene acetal 
• 111197-87-6 (S)-2-hydroxy-1-(4-methylphenyl)-1-propanone 2,2-dimethyl-trimethylene acetal 

Relevant academic research and scientific papers

Enantio- and regioselective reduction of α-diketones by baker's yeast

Although yeast reduction of α-diketones 1 affords a mixture of two α-hydroxy ketones and a vic-diol, the use of methyl vinyl ketone as an enzyme inhibitor prevents the production of the diol. Regioselectivity in the reduction to afford α-hydroxy ketones i

α-Hydroxylation of α,α-Disubstituted N-tert-Butanesulfinyl Ketimines with Molecular Oxygen: Stereoselective Synthesis of α-Tertiary Hydroxyimines

α-Tertiary hydroxyimines were stereoselectively synthesized from enantioenriched N-tert-butanesulfinyl ketimines using potassium tert-butoxide, molecular oxygen, and trimethyl phosphite. The stereoselective hydroxylation of acyclic ketimines bearing two sterically similar α-substituents was achieved by controlling the geometry of the metalloenamine intermediates and the facial selectivity of hydroxylation. The synthetic utility of the resulting α-tertiary hydroxyimines was demonstrated through the successful diastereoselective synthesis of highly substituted β-amino alcohols.

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.

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.

Asymmetric reduction of α-keto esters and α-diketones with a bakers' yeast keto ester reductase

Optically pure α-hydroxy esters and α-hydroxy ketones have been synthesized by the reduction of the corresponding ketones with a keto ester reductase isolated from bakers' yeast (YKER-I). The reduction of α-keto esters affords the corresponding (S)- or (R)-hydroxy esters selectively, where the stereochemical course depends on the chain length of the alkyl substituent on the carbonyl group. An α-keto short alkanoic ester affords the corresponding (S)-hydroxy ester, whereas a long alkanoate yields the corresponding (R)-hydroxy ester. The reduction of α-diketones affords the corresponding (S)-2-hydroxy ketones regio- and stereoselectively.

A General Synthetic Method of Chiral 2-Arylalkanoic Esters via Thermal 1,2-Rearrangement

(S)-1-Aryl-2-sulfonyloxy-1-alkanone acetals, prepared from natural ethyl (S)-lactate or (S)-valine (chiral sources) by the use of a Grignard reaction, were rearranged under hydrolytic conditions in the presence of a base to give (S)-2-arylalkanoic esters which in general, showed much higher pharmacological activities than their antipodes.