25297-16-9

Upstream product

• 622-47-9 4-tolylacetic acid 
• 18584-20-8 4-methylmandelic acid 
• 122-00-9 para-methylacetophenone 
• 104-87-0 4-methyl-benzaldehyde 
• 4815-10-5 2-hydroxy-2-(4-methylphenyl)acetonitrile 

Downstream Products

• 15674-78-9 (+/-)-α-bromo-p-tolylacetic acid ethyl ester 
• 77053-52-2 methyl bromo(4-methylphenyl)acetate 
• 530091-80-6 benzyl 2-bromo-2-(p-tolyl)acetate 

Relevant academic research and scientific papers

Catalytic Asymmetric Conjugate Addition and Sulfenylation of Diarylthiazolidin-2,4-diones

This work reports the first application of diarylthiazolidin-2,4-diones as nucleophiles in asymmetric catalysis. By utilizing chiral amino acid-based (thio)urea-tertiary amines as the catalysts, we successively established asymmetric conjugate addition to nitroolefins and sulfenylation to N-(sulfanyl)-succinimides of diarylthiazolidin-2,4-diones. Two series of biologically important 5-aryl-5-substituted thiazolidin-2,4-diones were obtained with high enantio- and diastereoselectivities (up to >99% ee and >19:1 dr). The enantioenriched adducts were found to show satisfactory anticancer activities against three different cancer cell lines using the MTT assay. All of these successes depended on the development of a general and expedient synthetic strategy to provide diverse 5H-thiazolidin-2,4-diones.

Lipase-catalyzed enantioselective transesterification toward esters of 2-bromo-tolylacetic acids

Lipases from Candida antarctica, Pseudomonas cepacia and Rhizomucor miehei were tested in the resolution of seven racemic substrates belonging to the (RS)-2-bromo tolyl acetate ester category, but differing either in the position of the methyl substituent on the acyl part of the aromatic ring, or in the structure of the alkyl group. Lipase-catalyzed kinetic resolution via transesterification reaction between the ester and octanol in octane revealed that, of the three enzymes tested, P. cepacia lipase is the most efficient for resolution of the various racemates, with R-enantiopreference. In addition, the position of the methyl substituent was found to play a key role in governing the enantioselectivity of the reaction. Using P. cepacia lipase and 2-bromo-m/p-tolyl- or 2-bromophenylacetic acid esters E-values of 6.