26159-36-4Relevant articles and documents
Chemoenzymatic synthesis of (2S)-2-arylpropanols through a dynamic kinetic resolution of 2-arylpropanals with alcohol dehydrogenases
Galletti, Paola,Emer, Enrico,Gucciardo, Gabriele,Quintavalla, Arianna,Pori, Matteo,Giacomini, Daria
experimental part, p. 4117 - 4123 (2010/10/03)
We applied Horse Liver Alcohol Dehydrogenase (HLADH) to the enantioselective synthesis of six (2S)-2-arylpropanols, useful intermediates in the synthesis of Profens. The influence of substrate structure and reaction conditions on yields and enantioselectivity were investigated. The high yields and high enantioselectivity towards the (S)-enantiomer obtained in the bioreduction of 2-arylpropionic aldehydes, clearly indicate the achievement of a DKR process through a combination of an enzyme-catalyzed kinetic reduction with a chemical base-catalyzed racemization of the unreacted aldehydes. The racemization step is represented by the keto-enol equilibrium of the aldehyde and can be controlled by modulating pH and reaction conditions.
Probing the parallel kinetic resolution of 1-phenylethanol using quasi-enantiomeric oxazolidinone adducts
Coulbeck, Elliot,Eames, Jason
, p. 2313 - 2325 (2008/03/18)
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.
A modification of the asymmetric dihydroxylation approach to the synthesis of (S)-2-arylpropanoic acids
Ishibashi, Hiroyuki,Maeki, Momoe,Yagi, Junko,Ohba, Masashi,Kanai, Tae
, p. 6075 - 6080 (2007/10/03)
Catalytic hydrogenolysis of (S)-2-phenyl-1-2-propanediol (2), prepared by an asymmetric dihydroxylation of α-methylstyrene (1) with AD-mix-α, over Pearlman's catalyst gave (S)-2-phenyl-1-propanol (3). This method was applied to the synthesis of optically active 2-arylpropanoic acid antiinflammatory agents, (S)-ibuprofen (8) and (S)-naproxen (13).