252877-04-6Relevant articles and documents
Halohydrin dehalogenase-catalysed synthesis of fluorinated aromatic chiral building blocks
Dokli, Irena,Mil?i?, Nevena,Marin, Petra,Mikleni?, Marina Svetec,Sudar, Martina,Tang, Lixia,Bla?evi?, Zvjezdana Findrik,Elenkov, Maja Majeri?
, (2021/02/02)
Kinetic resolution of a series of fluorinated styrene oxide derivatives was studied using halohydrin dehalogenase. A mutant HheC-W249P catalysed nucleophilic ring-opening with azide and cyanide ions with excellent enantioselectivity (E-values up to >200), which gives access to various enantiopure β-substituted alcohols and epoxides. It was found that the enzyme tolerates substrates in concentrations over 50 mM. However, different side reactions were observed at elevated concentrations and with prolonged reaction time. The biocatalytic azidolysis and cyanolysis of racemic 4-trifluoromethylstyrene oxide were performed on preparative scale, affording (R)-2-azido-1-(4-trifluoromethyl-phenyl)-ethanol in 38% yield and 97% ee, and (S)-3-hydroxy-3-(4-trifluoromethyl-phenyl)-propionitrile in 30% yield and 98% ee.
Nitration of Halterman porphyrin: A new route for fine tuning chiral iron and manganese porphyrins with application in epoxidation and hydroxylation reactions using hydrogen peroxide as oxidant
Amiri, Nesrine,Le Maux, Paul,Srour, Hassan,Nasri, Habib,Simonneaux, Gérard
, p. 8836 - 8842 (2015/03/04)
A methodology is reported for the regioselective nitration of the phenyl groups of Halterman porphyrin, using NaNO2. These nitro-porphyrins can be reduced to aminoporphyrins and then N-dimethylated to give new optically active porphyrins. Applications to the asymmetric epoxidation of styrene derivatives by H2O2 to give optically active epoxides (ee up to 60%) and hydroxylation of alkanes to give optically active secondary alcohols (ee up to 69%) were carried out in organic solvents (dichloromethane/methanol) using chiral iron and manganese porphyrins as catalysts.
Enantioselective manganese-porphyrin-catalyzed epoxidation and C-H hydroxylation with hydrogen peroxide in water/methanol solutions
Srour, Hassan,Maux, Paul Le,Simonneaux, Gerard
experimental part, p. 5850 - 5856 (2012/07/14)
The asymmetric epoxidation of alkene and hydroxylation of arylalkane derivatives by H2O2 to give optically active epoxides (enantiomeric excess (ee) up to 68%) and alcohols (ee up to 57%), respectively, were carried out in water/methanol solutions using chiral water-soluble manganese porphyrins as catalysts.