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Constraining Asymmetric Organometallic Catalysts within Mesoporous Supports Boosts Their Enantioselectivity
Abstract
By constraining tethered asymmetric organometallic catalysts within the nanopores of silica supports so as to increase the interaction between the pore wall and the active center (and hence to restrict access of the reactant to the catalyst), a significant improvement in enantioselectivity is achieved. A schematic illustration of a cationic chiral, organometallic catalyst, [Rh(I)(COD)PMP] {(S)-(+)-1-(2-pyrrolidinylmethyl)-pyrrolidine and cyclooctadiene}, which is noncovalently anchored via a N-H...F hydrogen bond with the triflate ion, CF3SO3-, to the curved inner surface of a 38 A diameter pore of a silica support for the asymmetric hydrogenation of the C=O bond in methyl benzoylformate to the corresponding methyl mandelate is shown. Rh (purple); N (blue); H (white); F (green); C (gray); S (yellow); O (red).
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Citations
Cited by
Asymmetric Heterogeneous Catalysis
Heitbaum, M., Glorius, F., & Escher, I. (2006) · Angewandte Chemie International Edition · doi:10.1002/anie.200504212 · Cited by 675
Functionalized mesoporous SBA-15 silica: recent trends and catalytic applications
Verma, P., Kuwahara, Y., Mori, K., Raja, R., & Yamashita, H. (2020) · Nanoscale · doi:10.1039/d0nr00732c · Cited by 391
Self-citationChiral Synthesis on Catalysts Immobilized in Microporous and Mesoporous Materials
Li, C. (2004) · Catalysis Reviews · doi:10.1081/cr-200036734 · Cited by 357
Asymmetric Nanocatalysis: N‐Heterocyclic Carbenes as Chiral Modifiers of Fe3O4/Pd nanoparticles
Ranganath, K. V. S., Kloesges, J., Schäfer, A. H., & Glorius, F. (2010) · Angewandte Chemie International Edition · doi:10.1002/anie.201002782 · Cited by 337
Thomas, J. M., & Raja, R. (2008) · Accounts of Chemical Research · doi:10.1021/ar700217y · Cited by 277
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Metadata
- Authors
- Raja, R., Thomas, J. M., Jones, M. D., Johnson, B. F. G., & Vaughan, D. E. W.
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 2003-11-15
- Volume
- 125
- Issue
- 49
- Pages
- 14982-14983
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- OpenAlex
- W2051976424
- Cited by
- 200
- References
- 0
- FWCI
- 9.66
- Type
- journal article
- Language
- en
- Open access
- closed
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- Raja, R., Thomas, J. M., Jones, M. D., Johnson, B. F. G., & Vaughan, D. E. W. (2003). Constraining Asymmetric Organometallic Catalysts within Mesoporous Supports Boosts Their Enantioselectivity. Journal of the American Chemical Society. https://doi.org/10.1021/ja030381r
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