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Highly Enantioselective Conjugate Additions to α,β-Unsaturated Ketones Catalyzed by a (Salen)Al Complex
Abstract
Chiral (salen)Al complex 1a catalyzes the highly enantioselective conjugate addition of carbon- and nitrogen-based nucleophiles to acyclic alpha,beta-unsaturated ketones. This methodology is tolerant of substantial variation of the ketone structure, providing access to a wide range of useful chiral building blocks in high yield and enantiomeric excess. Synthetic manipulations of the conjugate addition products are demonstrated, including the straightforward preparation of beta-amino ketones and highly enantioenriched carbo- and heterocyclic compounds.
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Citations
Cited by
CuI‐Catalyzed Alkyne–Azide “Click” Cycloadditions from a Mechanistic and Synthetic Perspective
Bock, V. D., Hiemstra, H., & van Maarseveen, J. H. (2006) · European Journal of Organic Chemistry · doi:10.1002/ejoc.200500483 · Cited by 1,452
Deprotonative Metalation Using Ate Compounds: Synergy, Synthesis, and Structure Building
Mulvey, R. E., Mongin, F., Uchiyama, M., & Kondo, Y. (2007) · Angewandte Chemie International Edition · doi:10.1002/anie.200604369 · Cited by 553
Cyclic Carbonate Synthesis Catalysed by Bimetallic Aluminium–Salen Complexes
Clegg, W., Harrington, R. W., North, M., & Pasquale, R. (2010) · Chemistry – A European Journal · doi:10.1002/chem.201000030 · Cited by 391
Hoashi, Y., Okino, T., & Takemoto, Y. (2005) · Angewandte Chemie International Edition · doi:10.1002/anie.200500459 · Cited by 275
Lin, Q., Meloni, D., Pan, Y., Xia, M., Rodgers, J., Shepard, S., Li, M., Galya, L., Metcalf, B., Yue, T.-Y., et al. (2009) · Organic Letters · doi:10.1021/ol900350k · Cited by 171
Metadata
- Authors
- Taylor, M. S., Zalatan, D. N., Lerchner, A. M., & Jacobsen, E. N.
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 2005-01-06
- Volume
- 127
- Issue
- 4
- Pages
- 1313-1317
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- OpenAlex
- W2101733985
- Cited by
- 331
- References
- 0
- FWCI
- 19.45
- Type
- journal article
- Language
- en
- Open access
- closed
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- Taylor, M. S., Zalatan, D. N., Lerchner, A. M., & Jacobsen, E. N. (2005). Highly Enantioselective Conjugate Additions to α,β-Unsaturated Ketones Catalyzed by a (Salen)Al Complex. Journal of the American Chemical Society. https://doi.org/10.1021/ja044999s
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Contains information from the Semantic Scholar Academic Graph Datasets, made available under the ODC Attribution License (ODC-BY 1.0).
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