565176-99-0Relevant articles and documents
Enantioselective Reduction of Ketones and Synthesis of 2-Methyl-2,3-dihydro-1-benzofuran Catalyzed by Chiral Spiroborate Ester
Chopade, A. U.,Chopade, M. U.,Nikalje, M. D.,Patil, H. S.
, p. 611 - 618 (2021/06/02)
Abstract: Asymmetric reduction of homobenzylic ketones was achieved through the use of chiral spiroborate ester catalyst. The catalyst is applicable for both analytical and industrial purposes since it is not sensitive to air and moisture. A rapid synthetic route has been developed for the preparation of (S)-2-methyl-2,3-dihydro-1-benzofuran via enantioselective reduction of homobenzylic ketone in the presence of a chiral spiroborate catalyst as the key step.
Expanding the Substrate Specificity of Thermoanaerobacter pseudoethanolicus Secondary Alcohol Dehydrogenase by a Dual Site Mutation
Musa, Musa M.,Bsharat, Odey,Karume, Ibrahim,Vieille, Claire,Takahashi, Masateru,Hamdan, Samir M.
, p. 798 - 805 (2018/02/21)
Here, we report the asymmetric reduction of selected phenyl-ring-containing ketones by various single- and dual-site mutants of Thermoanaerobacter pseudoethanolicus secondary alcohol dehydrogenase (TeSADH). The further expansion of the size of the substrate binding pocket in the mutant W110A/I86A not only allowed the accommodation of substrates of the single mutants W110A and I86A within the expanded active site but also expanded the substrate range of the enzyme to ketones bearing two sterically demanding groups (bulky–bulky ketones), which are not substrates for the TeSADH single mutants. We also report the regio- and enantioselective reduction of diketones with W110A/I86A TeSADH and single TeSADH mutants. The double mutant exhibited dual stereopreference to generate the Prelog products most of the time and the anti-Prelog products in a few cases.
Kinetic and chemical resolution of different 1-phenyl-2-propanol derivatives
Kiss, Violetta,Egri, Gabriella,Balint, Jozsef,Ling, Istvan,Barkoczi, Jozsef,Fogassy, Elemer
, p. 2220 - 2234 (2007/10/03)
Seven chiral target molecules containing a hydroxy group have been resolved by both biocatalytic and chemical means. The lipase-catalyzed acylation mainly yielded the acylated derivative of the (R)-alcohols with moderate enantiomeric excess and the enantiopure (S)-alcohols. In the course of the chemical resolution, first the dicarboxylic acid monoesters of the target molecules were synthesized and the resolution of these monoesters was attempted by different homochiral bases. By re-resolution and/or optimization of the reaction time and/or recrystallization, respectively, each molecule was produced in very high enantiomeric purity.