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Mechanistic Investigation Leads to a Synthetic Improvement in the Hydrolytic Kinetic Resolution of Terminal Epoxides
Abstract
The mechanism of the hydrolytic kinetic resolution (HKR) of terminal epoxides was investigated by kinetic analysis using reaction calorimetry. The chiral (salen)Co-X complex (X = OAc, OTs, Cl) undergoes irreversible conversion to (salen)Co-OH during the course of the HKR and thus serves as both precatalyst and cocatalyst in a cooperative bimetallic catalytic mechanism. This insight led to the identification of more active catalysts for the HKR of synthetically useful terminal epoxides.
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Citations
Cites
Asymmetric Catalysis of Epoxide Ring-Opening Reactions
Jacobsen, E. N. (2000) · Accounts of Chemical Research · doi:10.1021/ar960061v · Cited by 1,261
Self-citation
Cited by
Darensbourg, D. J. (2007) · Chemical Reviews · doi:10.1021/cr068363q · Cited by 1,593
Efficiency in Nonenzymatic Kinetic Resolution
Vedejs, E., & Jure, M. (2005) · Angewandte Chemie International Edition · doi:10.1002/anie.200460842 · Cited by 747
Recent advances in CO2/epoxide copolymerization—New strategies and cooperative mechanisms
Klaus, S., Lehenmeier, M. W., Anderson, C. E., & Rieger, B. (2011) · Coordination Chemistry Reviews · doi:10.1016/j.ccr.2010.12.002 · Cited by 710
Catalytic Non‐Enzymatic Kinetic Resolution
Pellissier, H. (2011) · Advanced Synthesis & Catalysis · doi:10.1002/adsc.201100111 · Cited by 353
Ford, D. D., Nielsen, L. P. C., Zuend, S. J., Musgrave, C. B., & Jacobsen, E. N. (2013) · Journal of the American Chemical Society · doi:10.1021/ja408027p · Cited by 138
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Metadata
- Authors
- Nielsen, L. P. C., Stevenson, C. P., Blackmond, D. G., & Jacobsen, E. N.
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 2004-01-15
- Volume
- 126
- Issue
- 5
- Pages
- 1360-1362
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- OpenAlex
- W2017223027
- Cited by
- 394
- References
- 1
- FWCI
- 14.41
- Type
- journal article
- Language
- en
- Open access
- closed
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- Nielsen, L. P. C., Stevenson, C. P., Blackmond, D. G., & Jacobsen, E. N. (2004). Mechanistic Investigation Leads to a Synthetic Improvement in the Hydrolytic Kinetic Resolution of Terminal Epoxides. Journal of the American Chemical Society. https://doi.org/10.1021/ja038590z
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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.