50418-68-3Relevant articles and documents
Structure-Guided Regulation in the Enantioselectivity of an Epoxide Hydrolase to Produce Enantiomeric Monosubstituted Epoxides and Vicinal Diols via Kinetic Resolution
Hou, Xiao-Dong,Hu, Bo-Chun,Hu, Die,Lei, Yu-Qing,Rao, Yi-Jian,Wu, Min-Chen,Zhang, Dong
supporting information, p. 1757 - 1761 (2022/03/16)
Structure-guided microtuning of an Aspergillus usamii epoxide hydrolase was executed. One mutant, A214C/A250I, displayed a 12.6-fold enhanced enantiomeric ratio (E = 202) toward rac-styrene oxide, achieving its nearly perfect kinetic resolution at 0.8 M in pure water or 1.6 M in n-hexanol/water. Several other beneficial mutants also displayed significantly improved E values, offering promising biocatalysts to access 19 structurally diverse chiral monosubstituted epoxides (97.1 - ≥ 99% ees) and vicinal diols (56.2-98.0% eep) with high yields.
Asymmetric Epoxidation of Olefins Catalyzed by Substituted Aminobenzimidazole Manganese Complexes Derived from L-Proline
Lin, Jin,Sun, Wei,Tian, Jing,Xia, Chungu,Zhang, Jisheng
supporting information, (2021/11/16)
A family of manganese complexes [Mn(Rpeb)(OTf)2] (peb=1-(1-ethyl-1H-benzo[d]imidazol-2-yl)-N-((1-((1-ethyl-1H-benzo[d]imidazol-2-yl)methyl) pyrrolidin-2-yl)methyl)-N-methylmethanamine)) derived from L-proline has been synthesized and characterized, where R refers to the group at the diamine backbone. X-ray crystallographic analyses indicate that all the manganese complexes [Mn(Rpeb)(OTf)2] exhibit cis-α topology. These types of complexes are shown to catalyze the asymmetric epoxidation of olefins employing H2O2 as a terminal oxidant with up to 96% ee. Obviously, the R group of the diamine backbone can influence the catalytic activity and enantioselectivity in the asymmetric epoxidation of olefins. In particular, Mn(i-Prpeb)(OTf)2 bearing an isopropyl arm, cannot catalyze the epoxidation reaction with H2O2 as the oxidant. However, when PhI(OAc)2 is used as the oxidant instead, all the manganese complexes including Mn(i-Prpeb)(OTf)2 can promote the epoxidation reactions efficiently. Taken together, these results indicate that isopropyl substitution on the Rpeb ligand inhibits the formation of active Mn(V)-oxo species in the H2O2/carboxylic acid system via an acid-assisted pathway.
Olefins oxidation with molecular O2 in the presence of chiral Mn (III) salen complex supported on magnetic CoFe2O4@SiO2@CPTMS
Hemmat, Kaveh,Nasseri, Mohammad A.,Allahresani, Ali
, (2019/04/26)
In the present study, CoFe2O4@SiO2@CPTMS nanocomposite was synthesized and the homogeneous chiral Mn-salen complex was anchored covalently onto the surface of CoFe2O4@SiO2@CPTMS nanocomposite. The heterogeneous Mn-salen magnetic nanocatalyst (CoFe2O4@SiO2@CPTMS@ chiral Mn (III) Complex) was characterized by different techniques including transmission electron microscopy (TEM), Fourier transform infrared (FT-IR), vibrating sample magnetometer (VSM), scanning electron microscopy (SEM), powder X-ray diffraction (XRD) and thermogravimetric analysis (TGA). Then, the aerobic enantioselective oxidation of olefins to the corresponding epoxide was investigated in the presence of magnetic chiral CoFe2O4@SiO2@Mn (III) complex at ambient conditions within 90?min. The results showed the corresponding products were synthesized with excellent yields and selectivity. In addition, the heterogeneous CoFe2O4@SiO2@ CPTMS@ chiral Mn (III) complex has benefits such as high selectivity and comparable catalytic reactivity with its homogeneous analog as well as mild reaction condition, facile recovery, and recycling of the heterogeneous catalyst.