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Chiral Organic Ion Pair Catalysts Assembled Through a Hydrogen-Bonding Network
Abstract
Catalytic Assembly: Most asymmetric catalysts employed in organic chemistry are assembled through binding of chiral ligands to one or more metal ions. Uraguchi et al. (p. 120 , published online 27 August) show that a highly selective catalyst can assemble through hydrogen bonding from a small collection of small molecules in the absence of metals. In the solid state, the catalyst comprises a central chiral phosphonium cation bound to two phenol molecules, which in turn bind a charge-compensating phenoxide ion. In solution, an oxazolone derivative appears to be able to bind in place of the phenoxide, spurring its stereoselective addition to a broad range of esters.
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Citations
Cited by
Supramolecular Chirality in Self-Assembled Systems
Liu, M., Zhang, L., & Wang, T. (2015) · Chemical Reviews · doi:10.1021/cr500671p · Cited by 2,250
The Vinylogous Aldol and Related Addition Reactions: Ten Years of Progress
Casiraghi, G., Battistini, L., Curti, C., Rassu, G., & Zanardi, F. (2011) · Chemical Reviews · doi:10.1021/cr100304n · Cited by 521
Metadata
- Authors
- Uraguchi, D., Ueki, Y., & Ooi, T.
- Venue
- Science
- Published
- 2009-10-02
- Volume
- 326
- Issue
- 5949
- Pages
- 120-123
- ISSN
- 0036-8075 (ISSN-L)
- 1095-9203
- OpenAlex
- W1987736083
- Cited by
- 247
- References
- 0
- FWCI
- 9.10
- Type
- journal article
- Language
- en
- Open access
- closed
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- Uraguchi, D., Ueki, Y., & Ooi, T. (2009). Chiral Organic Ion Pair Catalysts Assembled Through a Hydrogen-Bonding Network. Science. https://doi.org/10.1126/science.1176758
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Bibliographic data: Semantic Scholar, OpenAlex, Crossref.
Contains information from the Semantic Scholar Academic Graph Datasets, made available under the ODC Attribution License (ODC-BY 1.0).
Semantic Scholar’s data is described in: Kinney, R., et al. (2023). The Semantic Scholar Open Data Platform. arXiv:2301.10140.
