144782-30-9

Upstream product

• 32147-13-0 3-(4-methylphenyl)-2-butenoic acid 
• 122-00-9 para-methylacetophenone 
• 94853-53-9 ethyl 3-(4-methylphenyl)-2-butenoate 
• 14271-34-2 β-methyl 4-methylphenylacrylic acid 
• 6305-61-9 ethyl (E)-3-p-tolylbut-2-enoate 

Downstream Products

• 144782-34-3 (E)-3-p-Tolyl-but-2-enoic acid diisopropylamide 
• 144782-31-0 2,2-Dimethyl-3-((E)-3-p-tolyl-but-2-enoyl)-succinic acid dimethyl ester 
• 750647-59-7 (3R)-3-mercapto-3-(4-methylphenyl) butyric acid methyl ester 
• 750647-47-3 (S)-N-[(3R)-3-(4-methylphenyl)-3-mercaptobutanoyl]-4-isopropyloxazolidin-2-one 
• 38142-58-4 (+/-)-ar-turmerone 
• 39724-80-6 ar-E-Atlantone 
• 144782-32-1 (E)-2,2-Dimethyl-4-oxo-6-p-tolyl-hept-5-enoic acid 
• 144782-33-2 2,2-Dimethyl-4-oxo-6-p-tolyl-heptanoic acid 
• 1201-85-0 (S)-3-(4-methylphenyl)butanoic acid 
• 93922-52-2 (R)-3-(4-methylphenyl)butanoic acid 

Relevant academic research and scientific papers

Diastereoselective hydrogenation of α,β-unsaturated but-2-enamides to access the chiral 3-(p-tolyl) butanoic acids

An alternative methodology for the synthesis of chiral 3-(p-tolyl) butanoic acids is presented. This was accomplished through the diastereoselective hydrogenation reaction of different chiral N-3-(p-tolyl) but-2-enamides, using Pd/C in EtOH, to produce the corresponding chiral N-3-(p-tolyl) butanamides with high chemical yields and moderate diastereomeric ratios. Removal of the chiral auxiliary from N-3-(p-tolyl) butanamides gave the respective enantiomerically pure acids.

Rhodium/bisphosphine-thiourea-catalyzed enantioselective hydrogenation of α,β-unsaturated: N -acylpyrazoles

We successfully extended our Rh/bisphosphine-thiourea (ZhaoPhos) catalytic system to asymmetric hydrogenation of α,β-unsaturated N-acylpyrazoles affording products with high yields and excellent enantioselectivities (up to 97% yield, 99% ee). The pyrazole

N-heterocyclic carbene-catalyzed cyclization of unsaturated acyl chlorides and ketones

A straightforward synthesis of optically active trifluoromethyl dihydropyranones and spirocyclic oxindole-dihydropyranones has been realized by the chiral N-heterocyclic carbenes-catalyzed cyclization of α,β- unsaturated β-methylacyl chlorides with activated trifluoromethyl ketones or isatin derivatives. Copyright

2,2-Dimethylsuccinic acid derivatives in isoprenoid synthesis: a 2,2-dimethylvinyl anion equivalent in the synthesis of ar-atlantone, ar-turmerone, and prenylated aromatic compounds

The anion of methyl 2,2-dimethylsuccinate was alkylated with benzylic bromides to give the corresponding 3-substituted-2,2-dimethylsuccinates.Hydrolysis to the dicarboxylic acids, followed by bisdecarboxylation with lead tetraacetate, afforded 1-aryl-3-methyl-2-butenes, which are model prenylated aromatic compounds.Acylation of methyl-2,2-dimethylsuccinate with E-3-(4'-methylphenyl)crotonyl chloride gave the substituted succinate 9.Hydrolysis of the ester groups and acid-catalyzed decarboxylation of the resulting β-ketoacid produced the keto acid 10, which was decarboxylated by the Kochi method, furnishing ar-atlantone.Hydrogenatio n of 10 yielded 12, which on similar decarboxylation afforded ar-turmerone.