Journal
CATALYSIS LETTERS
Volume 150, Issue 3, Pages 861-873Publisher
SPRINGER
DOI: 10.1007/s10562-019-02933-1
Keywords
Chiral epoxidation; Oxygen; Manganese porphyrin; Graphite oxide; Heterogeneous catalysis
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A chirality inducer was prepared by graphite oxide (GO) functionalization with enantiopure l-tartrate (GO*) and used as asymmetric support for a covalently-linked manganese porphyrine complex [Mn(TPyP)OAc]. The thereby obtained heterogeneous catalyst, GO*-[Mn(TPyP)OAc], showed excellent performance and ee-values of 92-99% for the asymmetric epoxidation of prochiral olefins with O-2 as oxidant and isobutyraldehyde as co-reductant in acetonitrile; linear terminal olefins with 54-76% conversion and quantitative conversion of aromatic olefins. The GO*-[Mn(TPyP)OAc] catalyst is highly active, recyclable, and at the same time simple and inexpensive to prepare with a chiral inducer from the chiral pool. The structure of the catalyst was elucidated by scanning electron microscopy (SEM), transmission electron microscopy (TEM), BET analysis, FT-IR, Raman, and photoluminescence spectroscopic methods. Graphic Graphite oxide functionalized with an enantiopure group was used as a chirality inducer and asymmetric support for a Mn-porphyrine complex. The thereby obtained heterogeneous catalyst is an excellent enantioselective catalyst for the epoxidation of prochiral olefins.
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