145679-15-8

Upstream product

• 67-56-1 methanol 
• 151061-74-4 (R)-(-)-2-(4'-methylphenyl)propionamide 
• 622-97-9 1-ethenyl-4-methylbenzene 
• 201230-82-2 carbon monoxide 
• 938-94-3 (R,S)-2-(4'-methylphenyl) propionic acid 
• 18107-18-1 diazomethyl-trimethyl-silane 
• 79443-97-3 methyl 2-(4-methylphenyl)propanoate 
• 5337-93-9 4'-methylpropiophenone 
• 624-31-7 4-tolyl iodide 
• 34880-70-1 [1-methoxyprop-1-enyloxy]trimethylsilane 
• 29148-27-4 diethyl 2-(4-methylphenyl)propane-1,3-dioate 
• 131605-39-5 Acetic acid (S)-3-hydroxy-2-p-tolyl-propyl ester 
• 122091-54-7 (R)-(+)-2-(4-methylphenyl)propanol 
• 145621-69-8 (R)-p-cymen-9-yl acetate 

Downstream Products

• 807331-97-1 (4S,2E)-ethyl 4-p-tolylpent-2-enoate 
• 122091-53-6 2-(4-methylphenyl)propanal 
• 25532-74-5 (+)-(S)-nuciferal 
• 3241-74-5 (S)-4-p-tolylpentanal 
• 19876-64-3 (S)-(+)-4-p-tolylpentan-1-ol 
• 3649-81-8 (S)-curcumene 
• 122091-54-7 (R)-(+)-2-(4-methylphenyl)propanol 

Relevant academic research and scientific papers

Enantioselective Hydrogen Atom Transfer: Discovery of Catalytic Promiscuity in Flavin-Dependent 'Ene'-Reductases

Flavin has long been known to function as a single electron reductant in biological settings, but this reactivity has rarely been observed with flavoproteins used in organic synthesis. Here we describe the discovery of an enantioselective radical dehalogenation pathway for α-bromoesters using flavin-dependent 'ene'-reductases. Mechanistic experiments support the role of flavin hydroquinone as a single electron reductant, flavin semiquinone as the hydrogen atom source, and the enzyme as the source of chirality.

Pd/Josiphos-catalyzed enantioselective α-arylation of silyl ketene acetals and mechanistic studies on transmetalation and enantioselection

Palladium/(4-MeO-3,5-MePh)2PF-Pcy2) catalyzed the enantioselective arylation of silyl ketene acetals with iodoarenes in the presence of TlOAc to promote transmetalation of silyl ketene acetals. The highest enantioselectivities giving α-arylesters up to 91% ee were achieved when (E)-1-methoxy-1-(trimethylsiloxy)propene (E/Z = 88/12) was used for the silyl ketene acetal. The effect on enantioselection of a chiral ligand is discussed on the basis of the X-ray structure of the palladium/(4-MeO-3,5- MePh)2PF-Pcy2) complex and results of DFT computational studies on mechanistic aspects of the catalytic cycle.

Rational design of CH/π interaction sites in a basic resolving agent

A novel synthetic basic resolving agent, cis-1-aminobenz[f]indan-2-ol (ABI), was rationally designed by introducing effective CH/π interaction sites to cis-1-aminoindan-2-ol (AI), whose chiral recognition ability has been reported from our laboratory. ABI was applicable to a wide variety of racemic arylalkanoic acids and showed moderate to excellent chiral recognition ability, which was obviously higher than that of AI. The fundamental and important role of CH/π interactions, such as tunable CH(sp2)/π and CH(sp 3)/π interactions, in the chiral recognition by ABI was revealed by X-ray crystallographic study.

Enantioselective synthesis of (+)-nuciferal, (+)-(E)-nuciferol and (+)-α-curcumene by chiral hydrogenesterification reaction

Using chiral hydrogenesterification reaction as the key step, the stereoselective synthesis of (+)-nuciferal 1, (+)-(E)-nuciferol 2 and (+)-a-curcumene 3 has been achieved.

Enantioselective hydrolysis of various racemic α-substituted arylacetonitriles using Rhodococcus sp. CGMCC 0497

The enantioselective hydrolysis of 17 racemic α-substituted arylacetonitriles by Rhodococcus sp. CGMCC 0497 is described. The corresponding (R)-amides and (S)-acids were obtained with excellent enantiomeric excess in most cases. The effect of steric and electronic factors on the outcome of the reactions are discussed here. The results prove that nitrile-converting enzymes are efficient tools for the synthesis of sterically unencumbered chiral α-arylpropionic acids and amides.

Microbial asymmetric decarboxylation of fluorine-containing arylmalonic acid derivatives

α-Methyl-α-(trifluoromethylphenyl)malonic acids have been incubated with Alcaligenes bronchisepticus to afford optically active α-arylpropionic acids.Generally, the chemical and optical yields of the reaction products were higher when the substituents on the aromatic ring were strongly electron-withdrawing.Decarboxylation of α-fluoro-α-phenylmalonic acid with the aid of the same bacterium afforded optically active α-fluoro-α-phenylacetic acid.

Enzyme catalyzed monohydrolysis of 2-aryl-1 3-propanediol diacetates. A study of structural effects of the aryl moiety on the enantioselectivity

PPL catalyzed monohydrolysis of 2-aryl substituted 13-propanediol diacetates afforded the corresponding monoacetates in acceptable to fair chemical and optical yields. Electronic effects in the aromatic ring were examined. Elaboration of some 2-arylpropanediol monoacetates to optically active 2-arylpropanols and propanoic acids was performed.