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Engineering Chiral Polyoxometalate Hybrid Metal–Organic Frameworks for Asymmetric Dihydroxylation of Olefins
Abstract
Chiral metal-organic frameworks (MOFs) with porous and tunable natures have made them feasible for performing a variety of chemical reactions as heterogeneous asymmetric catalysts. By incorporating the oxidation catalyst [BW12O40](5-) and the chiral group, L- or D-pyrrolidin-2-ylimidazole (PYI), into one single framework, the two enantiomorphs Ni-PYI1 and Ni-PYI2 were obtained via self-assembly, respectively. The channels of Ni-PYIs were enlarged through a guest exchange reaction to remove the cationic chiral templates and were well modulated with hydrophilic/hydrophobic properties to allow molecules of both H2O2 and olefin ingress and egress. The coexistence of both the chiral directors and the oxidants within a confined space provided a special environment for the formation of reaction intermediates in a stereoselective fashion with high selectivity. The resulting MOF acted as an amphipathic catalyst to prompt the asymmetric dihydroxylation of aryl olefins with excellent stereoselectivity.
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Cited by
Multifunctional metal–organic framework catalysts: synergistic catalysis and tandem reactions
Huang, Y.-B., Liang, J., Wang, X.-S., & Cao, R. (2017) · Chemical Society Reviews · doi:10.1039/c6cs00250a · Cited by 1,908
Chiral Metal–Organic Frameworks
Gong, W., Chen, Z., Dong, J., Liu, Y., & Cui, Y. (2022) · Chemical Reviews · doi:10.1021/acs.chemrev.1c00740 · Cited by 579
Bioinspired Framework Catalysts: From Enzyme Immobilization to Biomimetic Catalysis
Wang, K.-Y., Zhang, J., Hsu, Y.-C., Lin, H., Han, Z., Pang, J., Yang, Z., Liang, R.-R., Shi, W., & Zhou, H.-C. (2023) · Chemical Reviews · doi:10.1021/acs.chemrev.2c00879 · Cited by 490
Kaur, H., Devi, N., Siwal, S. S., Alsanie, W. F., Thakur, M. K., & Thakur, V. K. (2023) · ACS Omega · doi:10.1021/acsomega.2c07719 · Cited by 273
Li, B., Leng, K., Zhang, Y., Dynes, J. J., Wang, J., Hu, Y., Ma, D., Shi, Z., Zhu, L., Zhang, D., et al. (2015) · Journal of the American Chemical Society · doi:10.1021/jacs.5b01352 · Cited by 264
Metadata
- Authors
- Han, Q., He, C., Zhao, M., Qi, B., Niu, J., & Duan, C.
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 2013-07-03
- Volume
- 135
- Issue
- 28
- Pages
- 10186-10189
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- OpenAlex
- W2328070910
- Cited by
- 380
- References
- 0
- FWCI
- 21.68
- Type
- journal article
- Language
- en
- Open access
- closed
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- Han, Q., He, C., Zhao, M., Qi, B., Niu, J., & Duan, C. (2013). Engineering Chiral Polyoxometalate Hybrid Metal–Organic Frameworks for Asymmetric Dihydroxylation of Olefins. Journal of the American Chemical Society. https://doi.org/10.1021/ja401758c
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