80720-86-1

Upstream product

• 25145-43-1 2-phenylpropionyl chloride 
• 98-85-1 1-Phenylethanol 
• 219951-25-4 (+/-)-pentafluorophenyl 2-phenylpropionate 
• 492-37-5 hydratropic acid 
• 79121-16-7 (S,S)-Hydratropasaeure-1-phenylester 
• 79121-13-4 (R)-2-phenylpropionic acid-(R)-1-phenylethyl ester 
• 25145-43-1 (2S)-2-phenylpropionyl chloride 
• 3156-07-8 methyl phenyl ketene 
• 16837-38-0 nicotinic anhydride 
• 104013-15-2 2-phenylpropionic acid p-nitrophenyl ester 

Relevant academic research and scientific papers

Stereodivergent Protein Engineering of a Lipase to Access All Possible Stereoisomers of Chiral Esters with Two Stereocenters

Enzymatic stereodivergent synthesis to access all possible product stereoisomers bearing multiple stereocenters is relatively undeveloped, although enzymes are being increasingly used in both academic and industrial areas. When two stereocenters and thus four stereoisomeric products are involved, obtaining stereodivergent enzyme mutants for individually accessing all four stereoisomers would be ideal. Although significant success has been achieved in directed evolution of enzymes in general, stereodivergent engineering of one enzyme into four highly stereocomplementary variants for obtaining the full complement of stereoisomers bearing multiple stereocenters remains a challenge. Using Candida antarctica lipase B (CALB) as a model, we report the protein engineering of this enzyme into four highly stereocomplementary variants needed for obtaining all four stereoisomers in transesterification reactions between racemic acids and racemic alcohols in organic solvents. By generating and screening less than 25 variants of each isomer, we achieved >90% selectivity for all of the four possible stereoisomers in the model reaction. This difficult feat was accomplished by developing a strategy dubbed "focused rational iterative site-specific mutagenesis" (FRISM) at sites lining the enzyme's binding pocket. The accumulation of single mutations by iterative site-specific mutagenesis using a restricted set of rationally chosen amino acids allows the formation of ultrasmall mutant libraries requiring minimal screening for stereoselectivity. The crystal structure of all stereodivergent CALB variants, flanked by MD simulations, uncovered the source of selectivity.

Resolution of secondary arylalkyl alcohols using pentafluorophenyl 2-phenylbutanoate and zinc chloride

The resolution of racemic secondary arylalkyl alcohols using pentafluorophenyl 2-phenylbutanoate and zinc chloride is discussed. The levels of enantiomeric recognition were high leading to enantiomerically enriched alcohols in good yield.

Phosphorofluoridic acid-catalyzed condensation reaction of carboxylic acids with 1-arylalkyl alcohols leading to esters under solvent-free conditions

Phosphorofluoridic acid with an L-menthyl group catalyzed condensation reaction between carboxylic acids and 1-arylalkyl alcohols under solvent-free conditions to give esters in moderate to high yields. Results using aliphatic acids are shown. Copyright

Parallel kinetic resolution of racemic 1-phenylethanol using quasi-enantiomeric combinations of carboxylic acids mediated by N,N′-dicyclohexylcarbodiimide and 3,5-lutidine

The parallel kinetic resolution of racemic 1-phenylethanol using an equimolar combination of quasi-enantiomeric 2-arylpropionic and butanoic acids mediated by a N,N′-dicyclohexylcarbodiimide (DCC)/3,5-lutidine coupling is discussed. The levels of diastereoselectivity were high leading to separable quasi-enantiomeric esters in good yield.

A versatile, practical, and inexpensive reagent, pyridine-3-carboxylic anhydride (3-PCA), for condensation reactions

A highly useful method for the preparation of carboxylic esters and carboxamides from various carboxylic acids was established by using a novel condensing reagent, pyridine-3-carboxylic anhydride (3-PCA), in the presence of 4-(dimethylamino)pyridine as an activator. The reactions of various carboxylic acids with nucleophiles, such as alcohols or amines, afforded the corresponding carboxylic acids or carboxamides in good to high yields under mild conditions by using simple experimental procedure. In addition, it was confirmed that this protocol was applicable to a gram-scale synthesis and the by-products, including pyridine-3-carboxylic acid and pyridine-3-carboxylate (or pyridine-3- carboxamide) produced in situ, were easily removed by using a simple aqueous workup.

Parallel kinetic resolution of 1-phenylethanol using quasi-enantiomeric active esters

The parallel kinetic resolution of racemic 1-phenylethanol using an equimolar combination of quasi-enantiomeric pentafluorophenyl esters is discussed. The levels of diastereoselectivity were excellent (>88% de) leading to separable quasi-enantiomeric esters in good yields. Georg Thieme Verlag Stuttgart.

Pyridine-3-carboxylic anhydride (3-PCA): A versatile, practical, and inexpensive reagent for condensation reaction between carboxylic acids and alcohols

A synthesis of carboxylic esters from various carboxylic acids and alcohols is successfully carried out by using a condensation reagent, pyridine-3-carboxylic anhydride (3-PCA). This reaction materialized synthesis of various carboxylic esters to be carried out under mild conditions by simple experimental procedure. Copyright

Probing the parallel kinetic resolution of 1-phenylethanol using quasi-enantiomeric oxazolidinone adducts

The parallel kinetic resolution of racemic 1-phenylethanol using an equimolar combination of quasi-enantiomeric oxazolidinones is discussed. The levels of diastereoselectivity were high leading to separable quasi-enantiomeric esters in good yield.

OXIDATIVE DECARBOXYLATION OF CARBOXYLIC ACIDS BY IRON PORPHYRIN - IODOSYLBENZENE SYSTEM

An iodosylbenzene - iron tetraarylporphyrin catalyst system decarboxylated α-aryl carboxylic acids and α,α,α-trisubstituted acetic acids efficiently to give the corresponding alcohol and carbonyl derivatives.

THE REACTION OF METHYL PHENYL KETENE AND 1-PHENYL ETHANOL - OBSERVATION OF A NEGATIVE ENTHALPY OF ACTIVATION

The unusual activation parameters of the reactions of aryl methyl ketenes and α-arylethanoles (ΔH(activ.)=-0.9 to +0.3 kcal/mol; ΔS(activ.)=-68 to -17 e.u.) are interpreted by a two step mechanism via reversible formation of a small concentration of an intermediate addition complex.