78533-73-0Relevant articles and documents
Biocatalytic Desymmetrization of Prochiral 3-Aryl and 3-Arylmethyl Glutaramides: Different Remote Substituent Effect on Catalytic Efficiency and Enantioselectivity
Ao, Yu-Fei,Zhang, Li-Bin,Wang, Qi-Qiang,Wang, De-Xian,Wang, Mei-Xiang
supporting information, p. 4594 - 4603 (2018/10/31)
Catalyzed by an amidase-containing Rhodococcus erythropolis AJ270 microbial whole cell catalyst in neutral phosphate buffer at 30 °C, desymmetric hydrolysis of a series of prochiral 3-aryl and 3-arylmethylglutaramides efficiently afforded 3-substituted glutaric acid monoamides in up to 95% yield and >99.5% ee. Even far away from the reaction site, the substituents on the aryl still have a significant effect on the catalytic activity and enantioselectivity and different remote substituent effect was observed for the two types of substrates. The synthetic application of biocatalytic desymmetrization was demonstrated by the facile transformation of the obtained enantiopure (R)-3-substituted 4-carbamoylbutanoic acid products to chiral dihydroquinolinone and δ-lactone compounds. (Figure presented.).
Cyanomethylation during the Electroreduction of Aromatic Carbonyl Compounds in Acetonitrile
Abbot, Elaine M.,Bellamy, Anthony J.,Kerr, John B.,MacKirdy, Iain S.
, p. 425 - 430 (2007/10/02)
The formation of substituted 3-hydroxy-3-phenylpropiononitriles (II), cinnamonitriles (III), 3-phenylpropiononitriles (IV), and 3-phenylglutaronitriles (V) during the electroreduction of acetophenone, benzaldehyde, and benzophenone in acetonitrile has been studied.The factors which influence the distribution of these products and their importance relative to the 'normal' reduction products, pinacols (VII) and carbinols (VIII), have been identified; current density, temperature, and water concentration are the most important.The distribution of acetonitrile-derived products is compared with that found when the corresponding cinnamonitriles (III) are electroreduced.
