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Catalytic, Enantioselective Aldol Additions with Methyl and Ethyl Acetate O-Silyl Enolates: A Chiral Tridentate Chelate as a Ligand for Titanium(IV)
Abstract
Asymmetric catalysis of the Mukaiyama aldol reaction has been reported with complexes derived from Al, B, Sn(II), and \nTi(IV). The levels of asymmetric induction for the addition of propionate-, isobutyrate-, and acetate-derived silyl thioketene acetals to aldehydes parallel those obtained with chiral-auxiliary-based methodologies. However, silyl ketene acetals derived from O-alkyl acetates uniformly provide aldolates possessing lower levels of asymmetric induction. We have initiated a study aimed at the design and synthesis of chiral Ti(IV) complexes that catalyze the enantioselective Mukaiyama aldol of O-trimethylsilyl, O-methyl, and O-ethyl ketene acetals with aldehydes. We report herein a catalyst that consists of a tridentate ligand derived from 3, Ti(O'^iPr)_4, and 3,5-di-tert-butylsalicylic acid. This catalyst (2-5 mol %) furnishes aldol adducts in good yields and high levels of asymmetric induction (88-97% ee).
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Cited by
Nitrogen-Containing Ligands for Asymmetric Homogeneous and Heterogeneous Catalysis
Fache, F., Schulz, E., Tommasino, M. L., & Lemaire, M. (2000) · Chemical Reviews · doi:10.1021/cr9902897 · Cited by 928
Sigman, M. S., & Jacobsen, E. N. (1998) · Journal of the American Chemical Society · doi:10.1021/ja980139y · Cited by 910
Nonlinear Effects in Asymmetric Catalysis
Satyanarayana, T., Abraham, S., & Kagan, H. B. (2009) · Angewandte Chemie International Edition · doi:10.1002/anie.200705241 · Cited by 591
Current progress in the asymmetric aldol addition reaction
Palomo, C., Oiarbide, M., & García, J. M. (2004) · Chem. Soc. Rev. · doi:10.1039/b202901d · Cited by 465
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
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Metadata
- Authors
- Carreira, E. M., Singer, R. A., & Lee, W.
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 1994-09
- Volume
- 116
- Issue
- 19
- Pages
- 8837-8838
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- OpenAlex
- W2006862079
- Cited by
- 286
- References
- 0
- FWCI
- 9.86
- Type
- journal article
- Language
- en
- Open access
- closed
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- CoChat. (2026). Citation check: Catalytic, Enantioselective Aldol Additions with Methyl and Ethyl Acetate O-Silyl Enolates: A Chiral Tridentate Chelate as a Ligand for Titanium(IV). https://app.cochat.ai/papers/10.1021/ja00098a065
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- Carreira, E. M., Singer, R. A., & Lee, W. (1994). Catalytic, Enantioselective Aldol Additions with Methyl and Ethyl Acetate O-Silyl Enolates: A Chiral Tridentate Chelate as a Ligand for Titanium(IV). Journal of the American Chemical Society. https://doi.org/10.1021/ja00098a065
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