The DOI matches its Crossref record; 4 of the 4 references it cites were found in a registry or an index.
Dramatic Improvement of the Enantiomeric Excess in the Asymmetric Conjugate Addition Reaction Using New Experimental Conditions
Abstract
The asymmetric conjugate addition of dialkylzincs is usually performed with Cu(OTf)(2) in toluene. We show that by using a copper carboxylate in Et(2)O, THF, or EtOAc, we strongly improve the enantioselectivity with a given ligand. Ee values up to 99.1% could be reached with new ligands based on the induced atropisomerism of a simple biphenol unit. In addition, we show that the Lewis acid effect of Cu(OTf)(2) is not a significant.
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Citations
Cites
Phosphoramidites: Marvellous Ligands in Catalytic Asymmetric Conjugate Addition
Feringa, B. L. (2000) · Accounts of Chemical Research · doi:10.1021/ar990084k · Cited by 703
Enantioselective Copper-Catalyzed Conjugate Addition of Dialkyl Zinc to Nitro-Olefins
Alexakis, A., & Benhaïm, C. (2000) · Organic Letters · doi:10.1021/ol0059596 · Cited by 89
Self-citationKitamura, M., Miki, T., Nakano, K., & Noyori, R. (2000) · Bulletin of the Chemical Society of Japan · doi:10.1246/bcsj.73.999 · Cited by 77
Wendisch, V., & Sewald, N. (1997) · Tetrahedron Asymmetry · doi:10.1016/s0957-4166(97)00102-x · Cited by 48
Cited by
In the Golden Age of Organocatalysis
Dalko, P. I., & Moisan, L. (2004) · Angewandte Chemie International Edition · doi:10.1002/anie.200400650 · Cited by 2,595
Okino, T., Hoashi, Y., & Takemoto, Y. (2003) · Journal of the American Chemical Society · doi:10.1021/ja036972z · Cited by 1,430
Phosphoramidites: Privileged Ligands in Asymmetric Catalysis
Teichert, J. F., & Feringa, B. L. (2010) · Angewandte Chemie International Edition · doi:10.1002/anie.200904948 · Cited by 710
First Synthesis of a β2-Homoamino Acid by Enantioselective Catalysis
Rimkus, A., & Sewald, N. (2003) · Organic Letters · doi:10.1021/ol027252k · Cited by 98
Metadata
- Authors
- Alexakis, A., Benhaim, C., Rosset, S., & Humam, M.
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 2002-04-18
- Volume
- 124
- Issue
- 19
- Pages
- 5262-5263
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- OpenAlex
- W2007884545
- Cited by
- 277
- References
- 4
- FWCI
- 24.44
- Type
- journal article
- Language
- en
- Open access
- closed
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- Alexakis, A., Benhaim, C., Rosset, S., & Humam, M. (2002). Dramatic Improvement of the Enantiomeric Excess in the Asymmetric Conjugate Addition Reaction Using New Experimental Conditions. Journal of the American Chemical Society. https://doi.org/10.1021/ja025598k
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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.
