The DOI matches its Crossref record; 1 of the 1 references it cites were found in a registry or an index.
Enantio- and Diastereoselective Michael Reaction of 1,3-Dicarbonyl Compounds to Nitroolefins Catalyzed by a Bifunctional Thiourea
Abstract
We synthesized a new class of bifunctional catalysts bearing a thiourea moiety and an amino group on a chiral scaffold. Among them, thiourea 1e bearing 3,5-bis(trifluoromethyl)benzene and dimethylamino groups was revealed to be highly efficient for the asymmetric Michael reaction of 1,3-dicarbonyl compounds to nitroolefins. Furthermore, we have developed a new synthetic route for (R)-(-)-baclofen and a chiral quaternary carbon center with high enantioselectivity by Michael reaction. In these reactions, we assumed that a thiourea moiety and an amino group of the catalyst activates a nitroolefin and a 1,3-dicarbonyl compound, respectively, to afford the Michael adduct with high enantio- and diastereoselectivity.
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Citations
Cites
First Synthesis of a β2-Homoamino Acid by Enantioselective Catalysis
Rimkus, A., & Sewald, N. (2003) · Organic Letters · doi:10.1021/ol027252k · Cited by 98
Cited by
Asymmetric Catalysis by Chiral Hydrogen‐Bond Donors
Taylor, M. S., & Jacobsen, E. N. (2006) · Angewandte Chemie International Edition · doi:10.1002/anie.200503132 · Cited by 1,906
Kobayashi, S., Mori, Y., Fossey, J. S., & Salter, M. M. (2011) · Chemical Reviews · doi:10.1021/cr100204f · Cited by 988
Herrera, R. P., Sgarzani, V., Bernardi, L., & Ricci, A. (2005) · Angewandte Chemie International Edition · doi:10.1002/anie.200500227 · Cited by 465
Bui, T., Syed, S., & Barbas, C. F. (2009) · Journal of the American Chemical Society · doi:10.1021/ja903520c · Cited by 351
Metadata
- Authors
- Okino, T., Hoashi, Y., Furukawa, T., Xu, X., & Takemoto, Y.
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 2004-12-03
- Volume
- 127
- Issue
- 1
- Pages
- 119-125
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- OpenAlex
- W2949100507
- Cited by
- 1,061
- References
- 1
- FWCI
- 25.00
- Type
- journal article
- Language
- en
- Open access
- closed
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- Okino, T., Hoashi, Y., Furukawa, T., Xu, X., & Takemoto, Y. (2005). Enantio- and Diastereoselective Michael Reaction of 1,3-Dicarbonyl Compounds to Nitroolefins Catalyzed by a Bifunctional Thiourea. Journal of the American Chemical Society. https://doi.org/10.1021/ja044370p
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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.
