88129-74-2

Upstream product

• 64-17-5 ethanol 
• 938-79-4 (2R)-2-phenylbutanoic acid 
• 75-03-6 ethyl iodide 
• 119-43-7 ethyl 2-phenylbutanoate 
• 60577-21-1 ethyl α-bromo-α-phenylbutyrate 
• 74042-63-0 (R)-(-)-2-phenylbutyramide 
• 769-68-6 2-phenylbutanenitrile 

Downstream Products

• 88129-72-0 (α-phenylpropyl)-(tetramethyl-2,3,4,5)cyclopentadiene 
• 16460-75-6 (R)-2-phenyl-butan-1-ol 

Relevant academic research and scientific papers

Modeling and optimization of lipase-catalyzed hydrolysis for production of (S)-2-phenylbutyric acid enhanced by hydroxyethyl-β-cyclodextrin

An efficient reactive system was established to produce (S)-2-phenylbutyric acid (2-PBA) through the enzymatic enantioselective hydrolysis of 2-phenylbutyrate ester (2-PBAE) in aqueous medium. Lipase CALA from Canadian antarctica and hexyl 2-phenylbutyrate (2-PBAHE) were identified upon screening as the best enzyme and substrate, respectively. Adding hydroxyethyl-β-cyclodextrin (HE-β-CD) to improve the solubility of the substrate resulted in a 1.5 times increase in substrate conversion while retaining a high enantioselectivity compared with that when HE-β-CD was not added. The effects of lipase concentration, substrate concentration and HE-β-CD concentration, temperature, pH, and reaction time on enantiomeric excess and conversion rate were investigated, and the optimal conditions were identified using response surface methodology (RSM). Under the optimal conditions, namely 50 mg/mL lipase CALA, 30 mmol/L substrate, 60 mmol/L HE-β-CD, pH of 6.5, temperature of 83 °C and reaction time of 18 h, the enantiomeric excess and overall conversion rate were 96.05% and 27.28%, respectively. This work provides an efficient alternative method for improving the conversion of aromatic ester substrates by including β-cyclodextrin in an aqueous hydrolysis reaction system.

Manganese Catalyzed Hydrogenation of Enantiomerically Pure Esters

A manganese-catalyzed hydrogenation of esters has been accomplished with TONs up to 1000, using cheap, environmentally benign, potassium carbonate and simple alcohols as activator and solvent, respectively. The weakly basic conditions lead to good functional group tolerance and enable the hydrogenation of enantiomerically enriched α-chiral esters with essentially no loss of stereochemical integrity.

CHIRAL ORGANOSILICON HYDRIDES

The invention provides a method for enantioselectively reducing a prochiral carbon centred radical having one or more electron donor groups attached directly to the central prochiral carbon atom of the radical, and/or attached to a carbon atom within 1 to 4 atoms of the central prochiral carbon atom, comprising treating said radical with an activated chiral non-racemic organosilicon hydride in the presence of a Lewis acid. The invention also provides a novel class of activated chiral non-racemic organosilicon hydrides.

Single enantiomer free-radical chemistry - Lewis acid-mediated reductions of racemic halides using chiral non-racemic stannanes

Additions of one to two equivalents of Lewis acids that include magnesium salts to free-radical reduction reactions involving ester functionalized radicals and (1R,2S,5R)-menthyldiphenyltin hydride 4, bis((1R,2S,5R)-menthyl) phenyltin hydride 5, tris((1R,

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.

The quest for single-enantiomer outcomes in free-radical chemistry

A significant challenge facing free-radical chemists is in the area of stereocontrol, specifically the ability to control the direction of reagent attack at a prochiral radical. While significant inroads have been made in the area of diastereoselective ra

Remarkable Lewis acid mediated enhancement of enantioselectivity during free-radical reductions by simple chiral non-racemic stannanes

Additions of 1 equiv, of achiral and chiral Lewis acids to free-radical reduction reactions involving (1S,2S,5R)-menthyldiphenyltin hydride 1, bis[(1S,2S,5R)-menthyl]phenyltin hydride 2, bis[1S,2S,5R)-menthyl][8-(N,N-dimethylamino)naphthyl]tin hydride 3, bis[(1R,2S,5R-menthyl] {1-(S)-N,N-dimethylaminoethyl]phenyl}tin hydride 4 or 3α-dimethylstannyl-5α-cholestane 5 result in remarkable increases in enantioselectivity.

An improved method for preparation of carboxylic esters using CsF- celite/alkyl halide/CH3CN combination

A new method for efficient and chemoselective esterification of carboxylic acids in CsF-Celite/alkyl halide/CH3CN reaction system is described.