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Enantioselective Polymerization of Epoxides: A Highly Active and Selective Catalyst for the Preparation of Stereoregular Polyethers and Enantiopure Epoxides
Abstract
A chiral, bimetallic cobalt catalyst was discovered that is highly active and enantioselective for epoxide polymerization. The enantiomerically pure catalyst system exhibits a stereoselectivity factor (s = k(fast)/k(slow)) of 370 for propylene oxide, allowing enantiomerically pure epoxide to be recovered in nearly the maximum theoretical yield. In addition, the racemic catalyst forms highly isotactic poly(propylene oxide) in quantitative yield. The catalyst is active and selective for other epoxides, such as 1-butene oxide, 1-hexene oxide, and styrene oxide.
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Cites
Moore, D. R., Cheng, M., Lobkovsky, E. B., & Coates, G. W. (2003) · Journal of the American Chemical Society · doi:10.1021/ja030085e · Cited by 515
Self-citationBraune, W., & Okuda, J. (2003) · Angewandte Chemie International Edition · doi:10.1002/anie.200390054 · Cited by 114
Cited by
A rational strategy for the realization of chain-growth supramolecular polymerization
Kang, J., Miyajima, D., Mori, T., Inoue, Y., Itoh, Y., & Aida, T. (2015) · Science · doi:10.1126/science.aaa4249 · Cited by 665
Stereoselective Epoxide Polymerization and Copolymerization
Childers, M. I., Longo, J. M., Van Zee, N. J., LaPointe, A. M., & Coates, G. W. (2014) · Chemical Reviews · doi:10.1021/cr400725x · Cited by 471
Self-citationStereochemical enhancement of polymer properties
Worch, J. C., Prydderch, H., Jimaja, S., Bexis, P., Becker, M. L., & Dove, A. P. (2019) · Nature Reviews Chemistry · doi:10.1038/s41570-019-0117-z · Cited by 336
Recent advances in cooperative bimetallic asymmetric catalysis: dinuclear Schiff base complexes
Matsunaga, S., & Shibasaki, M. (2014) · Chem. Commun. · doi:10.1039/c3cc47587e · Cited by 263
Auriemma, F., De Rosa, C., Di Caprio, M. R., Di Girolamo, R., Ellis, W. C., & Coates, G. W. (2015) · Angewandte Chemie International Edition · doi:10.1002/anie.201410211 · Cited by 164
Self-citationRobert, C., Schmid, T. E., Richard, V., Haquette, P., Raman, S. K., Rager, M.-N., Gauvin, R. M., Morin, Y., Trivelli, X., Guérineau, V., et al. (2017) · Journal of the American Chemical Society · doi:10.1021/jacs.7b01749 · Cited by 101
Isotactic Poly(propylene oxide): A Photodegradable Polymer with Strain Hardening Properties
Lipinski, B. M., Morris, L. S., Silberstein, M. N., & Coates, G. W. (2020) · Journal of the American Chemical Society · doi:10.1021/jacs.0c01768 · Cited by 73
Self-citationNielsen, L. P. C., Zuend, S. J., Ford, D. D., & Jacobsen, E. N. (2012) · The Journal of Organic Chemistry · doi:10.1021/jo300181f · Cited by 62
Metadata
- Authors
- Hirahata, W., Thomas, R. M., Lobkovsky, E. B., & Coates, G. W.
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 2008-12-09
- Volume
- 130
- Issue
- 52
- Pages
- 17658-17659
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- OpenAlex
- W1975602988
- Cited by
- 198
- References
- 2
- FWCI
- 6.44
- Type
- journal article
- Language
- en
- Open access
- closed
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