Highly enantioselective epoxidation of unfunctionalized olefins catalyzed by chiral jacobsen's catalyst immobilized on phenoxy-modified zirconium poly(syrene-phenylvinylphosphonate)phosphate

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Abstract

Chiral Jacobsen's catalyst was axially immobilized onto phenoxy-modified zirconium poly(styrene-phenylvinylphosphonate)phosphate (ZPS-PVPA). The immobilized catalysts show comparable ee values for asymmetric epoxidation of styrene and much higher ee values for a-methylstyrene (73.7% vs. 54.0%) and indene (99.9% vs. 65.0%) than the homogeneous Jacobsen's catalyst. Moreover, the assynthesized catalysts are relatively stable and can be recycled at least five times without significant loss of activity and enantioselectivity. A point worth emphasizing is that the heterogeneous catalysts afforded remarkable increases of conversion and ee values in the absence of expensive O-coordinating axial bases for the asymmetric epoxidation of olefins, especially for the epoxidation of α-methylstyrene (conversion: from 24.3% to 99.9%; ee: from 29.4% to 73.7%), which may overcome the last obstacle for the potential industry application of chiral Jacobsen's catalyst. © 2010 Wiley-VCH Verlag GmbH & Co. KGaA.

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Zou, X., Fu, X., Li, Y., Li, X., Fu, S., Luo, Y., & Wu, X. (2010). Highly enantioselective epoxidation of unfunctionalized olefins catalyzed by chiral jacobsen’s catalyst immobilized on phenoxy-modified zirconium poly(syrene-phenylvinylphosphonate)phosphate. Advanced Synthesis and Catalysis, 352(1), 163–170. https://doi.org/10.1002/adsc.200900424

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