The DOI matches its Crossref record.
Highly Enantioselective Direct Conjugate Addition of Ketones to Nitroalkenes Promoted by A Chiral Primary Amine−Thiourea Catalyst
Abstract
Primary amine-thiourea derivative 1 is an active and highly enantioselective catalyst for the conjugate addition of ketones to nitroalkenes. Broad substrate scope is described, with nitroalkenes bearing either aromatic or aliphatic substituents and a wide variety of ketones shown to be useful reacting partners. Ethyl ketones react preferentially, generating anti products with methyl-bearing stereocenters with good-to-excellent diastereoselectivity. An enamine mechanism is indicated, with cooperative activation of the electrophile by the thiourea and of the ketone by the primary amine.
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Citations
Cited by
Small-Molecule H-Bond Donors in Asymmetric Catalysis
Doyle, A. G., & Jacobsen, E. N. (2007) · Chemical Reviews · doi:10.1021/cr068373r · Cited by 2,608
Self-citationAsymmetric Aminocatalysis—Gold Rush in Organic Chemistry
Melchiorre, P., Marigo, M., Carlone, A., & Bartoli, G. (2008) · Angewandte Chemie International Edition · doi:10.1002/anie.200705523 · Cited by 1,256
Bui, T., Syed, S., & Barbas, C. F. (2009) · Journal of the American Chemical Society · doi:10.1021/ja903520c · Cited by 351
Wang, X., Liu, J., Xu, S., Xu, J., Pan, X., Liu, J., Cui, S., Li, Z., & Guo, K. (2016) · Polymer Chemistry · doi:10.1039/c6py01107a · Cited by 50
Metadata
- Authors
- Huang, H., & Jacobsen, E. N.
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 2006-05-12
- Volume
- 128
- Issue
- 22
- Pages
- 7170-7171
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- OpenAlex
- W2032232114
- Cited by
- 446
- References
- 0
- FWCI
- 31.11
- Type
- journal article
- Language
- en
- Open access
- closed
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