24716-09-4

Upstream product

• 859197-71-0 phenyl-n-butylmalonic acid 
• 88733-46-4 ethyl α-bromo-α-phenylhexanoate 
• 41961-73-3 2-Phenyl-capronsaeure-tert-butylester 
• 109-65-9 1-bromo-butane 
• 103-82-2 phenylacetic acid 
• 16537-09-0 t-butyl phenylacetate 
• 124-38-9 carbon dioxide 
• 83-13-6 diethyl 2-phenylmalonate 
• 7155-21-7 diethyl phenyl-n-butylmalonate 

Downstream Products

• 21490-48-2 (S)-(+)-2-phenylhexanoic acid 
• 116032-02-1 2-phenyl-hexanoic acid 2,2'-piperazine-1,4-diyl-diethyl ester 
• 5636-59-9 2-phenyl-hex-2-enoic acid 
• 61501-03-9 α-n-butylbenzylamine 
• 104447-46-3 3-Methoxy-4-[6-(2-phenyl-hexanoylamino)-indol-1-ylmethyl]-benzoic acid methyl ester 
• 60972-86-3 2-phenylhexanoyl chloride 
• 27059-47-8 1-phenyl-1-chloropentane 
• 64498-08-4 n-butylphenylketene 
• 14072-67-4 2-phenylhexanamide 

Relevant academic research and scientific papers

Isothiourea-Catalyzed Acylative Kinetic Resolution of Tertiary α-Hydroxy Esters

A highly enantioselective isothiourea-catalyzed acylative kinetic resolution (KR) of acyclic tertiary alcohols has been developed. Selectivity factors of up to 200 were achieved for the KR of tertiary alcohols bearing an adjacent ester substituent, with both reaction conversion and enantioselectivity found to be sensitive to the steric and electronic environment at the stereogenic tertiary carbinol centre. For more sterically congested alcohols, the use of a recently-developed isoselenourea catalyst was optimal, with equivalent enantioselectivity but higher conversion achieved in comparison to the isothiourea HyperBTM. Diastereomeric acylation transition state models are proposed to rationalize the origins of enantiodiscrimination in this process. This KR procedure was also translated to a continuous-flow process using a polymer-supported variant of the catalyst.

Ruthenium-catalyzed umpolung carboxylation of hydrazones with CO2

The first ruthenium-catalyzed umpolung carboxylation of hydrazones with CO2 to generate important aryl acetic acids is reported. Besides aldehyde hydrazones, a variety of ketone hydrazones, which have not been successfully applied in previous umpolung reactions with other reactive electrophiles, also show high reactivity and selectivity under mild conditions. Moreover, this operationally simple protocol features good functional group tolerance, is readily scalable, and offers easy derivation of important structures, including bioactive felbinac and adiphenine. Computational studies reveal that this umpolung reaction proceeds through the generation of a Ru-nitrenoid followed by concerted [4 + 2] cycloaddition with CO2.

N-heterocyclic carbene-mediated enantioselective addition of phenols to unsymmetrical alkylarylketenes

Chiral N-heterocyclic carbenes (NHCs) mediate the enantioselective addition of 2-phenylphenol to unsymmetrical alkylarylketenes, delivering α-alkyl-α-arylacetic acid derivatives with good levels of enantiocontrol (up to 84% ee). Enantiodivergent stereochemical outcomes are observed using 2-phe-nylphenol and benzhydrol in the NHC-promoted esterification reaction using a triazolium precatalyst derived from pyroglutamic acid, consistent with distinct mechanistic pathways operating within these processes.

New conditions for the generation of dianions of carboxylic acids

Lithium carboxylic acid enediolates are generated efficiently using lithium amides prepared from thienyllithium or butyllithium and either diethylamine, piperazine, N,N'-dibenzylethylenediamine, N-benzylpiperazine or 1,3,3-trimethyl-6-azabicyclo[3.2.1]oct

OXIDATIVE COUPLING REACTIONS UNDER PTC CONDITIONS

Succinic acid derivatives have been prepared from cyanohalides under PTC conditions in good yields.