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Chiral Bis(oxazoline) Copper(II) Complexes: Versatile Catalysts for Enantioselective Cycloaddition, Aldol, Michael, and Carbonyl Ene Reactions
Abstract
A bis(oxazoline) (box) copper(II) complex and its hydrated counterpart (1 and 2) function as enantioselective Lewis acid catalysts for carbocyclic and hetero Diels-Alder, aldol, Michael, ene, and amination reactions with substrates capable of chelation through six- and five-membered rings. X-ray crystallography of the chiral complexes reveals a propensity for the formation of distorted square planar or square pyramidal geometries. The sense of asymmetric induction is identical for all the processes catalyzed by [Cu((S,S)-t-Bu-box)](X)(2) complexes 1 and 2 (X = OTf and SbF) resulting from the intervention of a distorted square planar catalyst-substrate binary complex. These catalyzed processes exhibit excellent temperature-selectivity profiles. Reactions catalyzed by [Cu(S,S-Ph-pybox)](SbF(6))(2) and their derived chelation complexes are also discussed.
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Cites
637. The stability of transition-metal complexes
Irving, H., & Williams, R. J. P. (1953) · Journal of the Chemical Society (Resumed) · doi:10.1039/jr9530003192 · Cited by 2,116
Cited by
Parmar, D., Sugiono, E., Raja, S., & Rueping, M. (2014) · Chemical Reviews · doi:10.1021/cr5001496 · Cited by 2,118
Hydroamination: Direct Addition of Amines to Alkenes and Alkynes
Müller, T. E., Hultzsch, K. C., Yus, M., Foubelo, F., & Tada, M. (2008) · Chemical Reviews · doi:10.1021/cr0306788 · Cited by 2,090
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
Ion Pairing in Transition-Metal Organometallic Chemistry
Macchioni, A. (2005) · Chemical Reviews · doi:10.1021/cr0300439 · Cited by 549
Enantioselective Chemo‐ and Biocatalysis: Partners in Retrosynthesis
Hönig, M., Sondermann, P., Turner, N. J., & Carreira, E. M. (2017) · Angewandte Chemie International Edition · doi:10.1002/anie.201612462 · Cited by 284
Metadata
- Authors
- Johnson, J. S., & Evans, D. A.
- Venue
- Accounts of Chemical Research
- Publisher
- American Chemical Society (ACS)
- Published
- 2000-01-19
- Volume
- 33
- Issue
- 6
- Pages
- 325-335
- ISSN
- 0001-4842 (ISSN-L)
- 1520-4898
- OpenAlex
- W2118928564
- Cited by
- 1,046
- References
- 1
- FWCI
- 43.86
- Type
- journal article
- Language
- en
- Open access
- closed
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- Johnson, J. S., & Evans, D. A. (2000). Chiral Bis(oxazoline) Copper(II) Complexes: Versatile Catalysts for Enantioselective Cycloaddition, Aldol, Michael, and Carbonyl Ene Reactions. Accounts of Chemical Research. https://doi.org/10.1021/ar960062n
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