7476-63-3Relevant articles and documents
One-pot method for the synthesis of 1-aryl-2-aminoalkanol derivatives from the corresponding amides or nitriles
Bobal, Pavel,Otevrel, Jan,Svestka, David
, p. 25029 - 25045 (2020/07/14)
We have identified a novel one-pot method for the synthesis of β-amino alcohols, which is based on C-H bond hydroxylation at the benzylic α-carbon atom with a subsequent nitrile or amide functional group reduction. This cascade process uses molecular oxygen as an oxidant and sodium bis(2-methoxyethoxy)aluminum hydride as a reductant. The substrate scope was examined on 30 entries and, although the respective products were provided in moderate yields only, the above simple protocol may serve as a direct and powerful entry to the sterically congested 1,2-amino alcohols that are difficult to prepare by other routes. The plausible mechanistic rationale for the observed results is given and the reaction was applied to a synthesis of a potentially bioactive target. This journal is
Enantioselective biotransformations of racemic α-substituted phenylacetonitriles and phenylacetamides using Rhodococcus sp. AJ270
Wang, Mei-Xiang,Lu, Gang,Ji, Gai-Jiao,Huang, Zhi-Tang,Meth-Cohn, Otto,Colby, John
, p. 1123 - 1135 (2007/10/03)
Rhodococcus sp. AJ270 is an efficient whole-cell system able to catalyze the stereoselective conversions of racemic α-substituted phenylacetonitriles and amides under very mild conditions into enantiopure carboxylic acids and derivatives. The nitrile hydratase involved generally has a broad substrate spectrum against phenylacetonitriles irrespective of the electronic nature of the α-substituent while the amidase is very sensitive to both the electronic and steric factors of the substituent of amides. The overall enantioselectivity of nitrile hydrolysis is mainly determined by the combination of selectivities of nitrile hydratase and of amidase, with the latter being a major contributor. The amidase has high S-enantiocontrol against amides while the nitrile hydratase exhibits low R-selectivity against nitriles. The scope and limitations of this enantioselective biotransformation process are discussed. Copyright (C) 2000 Elsevier Science Ltd.
The Chemistry of 5-Oxodihydroisoxales. XI; The Photolysis of 3-Hydroxy-4-phenylisoxazol-5(2H)-ones (Phenyldisic Acids)
Prager, Rolf H.,Smith, Jason A.
, p. 217 - 226 (2007/10/02)
3-Hydroxy-2-methyl-4-phenylisoxazol-5(2H)-one, 3-hydroxy-2,4-diphenylisoxazol-5(2H)-one and phenyldisic acid have been photolysed at 254 nm in hydroxylic solvents.By comparision of the respective products with those obtained from 3-methoxy-4-phenylisoxazo
