293731-49-4

Upstream product

• 100-51-6 benzyl alcohol 
• 405-50-5 p-Fluorophenylacetic acid 
• 100-39-0 benzyl bromide 
• 702-11-4 4-fluoro-N,N-dimethylbenzylamine 
• 201230-82-2 carbon monoxide 
• 459-04-1 4-Fluorophenylacetyl chloride 
• 1090480-39-9 N-(benzyloxy)-2-(4-fluorophenyl)acetamide 
• 108-88-3 toluene 

Downstream Products

• 293731-51-8 (RS)-benzyl 2-(4-fluorophenyl)-3-phthalimidopropanoate 
• 512176-77-1 benzyl 2-benzoyl-2-(4-fluorophenyl)ethanoate 
• 293731-64-3 (αS,3'R)-4',4'-dimethyl-γ-butyrolacton-3'-yl 2-(4-fluorophenyl)-3-phthalimidopropanoate 
• 267001-10-5 (αR,3'R)-4',4'-dimethyl-γ-butyrolacton-3'-yl 2-(4-fluorophenyl)-3-phthalimidopropanoate 
• 293731-59-6 (RS)-3-phthalimido-2-(4-fluorophenyl)propanoic acid chloride 
• 293731-55-2 (RS)-2-(4-fluorophenyl)-3-phthalimidopropanoic acid 
• 512176-89-5 benzyl 2-benzoyl-2-(4-fluorophenyl)propanoate 

Relevant academic research and scientific papers

Palladium-catalyzed carbonylation of benzylic ammonium salts to amides and esters: Via C-N bond activation

An efficient palladium-catalyzed carbonylation reaction of readily available quaternary ammonium salts with CO is reported for the first time to afford arylacetamides and arylacetic acid esters via benzylic C-N bond cleavage. This protocol features mild reaction conditions under atmospheric pressure of CO, a redox-neutral process without an additional oxidant, and a broad substrate scope for various kinds of amines, alcohols and phenols.

Palladium-catalyzed benzylation of carboxylic acids with toluene via benzylic C-H activation

Direct benzylation of carboxylic acids with toluene has been developed via palladium-catalyzed C-H acyloxylation under 1 atm of oxygen. This reaction demonstrates good functional group tolerance and high yields, providing a facile, atom-economic, and efficient method for the synthesis of benzyl esters.

Direct conversion of N -alkoxyamides to carboxylic esters through tandem nbs-mediated oxidative homocoupling and thermal denitrogenation

Treatment of N-alkoxyamides with NBS in toluene was found to conveniently afford the corresponding carboxylic esters, including those bearing a bulky or long-chain substituent, in satisfactory to excellent yields. This approach not only represents a convenient and economic approach to a direct transformation of an alkoxyamide moiety into the carboxylic ester functional group, via oxidative homocoupling and the subsequent thermal denitrogenation, but also facilitates the synthesis of sterically hindered carboxylic esters.

Catalysed asymmetric protonation of simple linear keto-enolic species a route to chiral α-arylpropionic acids

The reaction cascade consisting of deprotection/decarboxylation/asymmetric protonation of enolic species, starting from open-chain benzyl β-oxo esters, has been studied. When carried out in the presence of catalytic amounts of cinchonine, the reaction gave optically active α-aryl ketones with up to 75% ee. Enantio-enriched (S)-3-phenyl-2-butanone can be converted into 2-phenylpropionic acid without racemisation. Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002.

Asymmetric synthesis of (S)-β2-homoarylglycines

The synthesis of racemic N-phthalyl β2-homoarylglycines 5 and their asymmetric transformation have been investigated. The key step is the stereoselective addition of the (R)-pantolactone to the corresponding prochiral ketene 7.