The DOI matches its Crossref record; 1 of the 1 references it cites were found in a registry or an index.
A Homochiral Metal–Organic Framework as an Effective Asymmetric Catalyst for Cyanohydrin Synthesis
Abstract
A homochiral metal-organic framework (MOF) of an enantiopure 2,2'-dihydroxy-1,1'-biphenyl ligand was constructed. After exchanging one proton of the dihydroxyl group for Li(I) ions, the framework is shown to be a highly efficient and recyclable heterogeneous catalyst for asymmetric cyanation of aldehydes with up to >99% ee. Compared with the homogeneous counterpart, the MOF catalyst exhibits significantly enhanced catalytic activity and enantioselectivity, especially at a low catalyst/substrate ratio, due to that the rigid framework could stabilize the catalytically active monolithium salt of biphenol against its free transformation to catalytically inactive and/or less active assemblies in reactions. The synthetic utility of the cyanation was demonstrated in the synthesis of (S)-bufuralol (a nonselective β-adrenoceptor blocking agent) with 98% ee.
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Cites
Metal-organic framework materials as catalysts
Lee, J., Farha, O. K., Roberts, J., Scheidt, K. A., Nguyen, S. T., & Hupp, J. T. (2009) · Chemical Society Reviews · doi:10.1039/b807080f · Cited by 7,969
Cited by
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
Self-citationLi, 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
- Mo, K., Yang, Y., & Cui, Y.
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 2014-01-21
- Volume
- 136
- Issue
- 5
- Pages
- 1746-1749
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- OpenAlex
- W1988731900
- Cited by
- 256
- References
- 1
- FWCI
- 19.33
- Type
- journal article
- Language
- en
- Open access
- closed
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