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Enantioselective Construction of Spirocyclic Oxindolic Cyclopentanes by Palladium-Catalyzed Trimethylenemethane-[3+2]-Cycloaddition
Open accessAbstract
The palladium catalyzed [3+2] trimethylenemethane (TMM) cycloaddition is an efficient method for the construction of cyclopentanes. Herein, we report a catalytic asymmetric protocol for the synthesis of spirocyclic oxindolic cyclopentanes in excellent yields and enantioselectivities, allowing for the first time the construction of up to three adjacent stereogenic centers. In this process, the chiral ligand controls the diastereo- as well as enantioselectivity.
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Citations
Cited by
Zhou, F., Liu, Y., & Zhou, J. (2010) · Advanced Synthesis & Catalysis · doi:10.1002/adsc.201000161 · Cited by 1,252
Phosphoramidites: Privileged Ligands in Asymmetric Catalysis
Teichert, J. F., & Feringa, B. L. (2010) · Angewandte Chemie International Edition · doi:10.1002/anie.200904948 · Cited by 710
Bencivenni, G., Wu, L., Mazzanti, A., Giannichi, B., Pesciaioli, F., Song, M., Bartoli, G., & Melchiorre, P. (2009) · Angewandte Chemie International Edition · doi:10.1002/anie.200903192 · Cited by 448
Liu, Y., Nappi, M., Arceo, E., Vera, S., & Melchiorre, P. (2011) · Journal of the American Chemical Society · doi:10.1021/ja206517s · Cited by 398
Catalytic Enantioselective Construction of Spiro Quaternary Carbon Stereocenters
Xu, P.-W., Yu, J.-S., Chen, C., Cao, Z.-Y., Zhou, F., & Zhou, J. (2019) · ACS Catalysis · doi:10.1021/acscatal.8b03694 · Cited by 325
Metadata
- Authors
- Trost, B. M., Cramer, N., & Silverman, S. M.
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 2007-09-20
- Volume
- 129
- Issue
- 41
- Pages
- 12396-12397
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- OpenAlex
- W2000266008
- Cited by
- 420
- References
- 0
- FWCI
- 9.12
- Type
- journal article
- Language
- en
- Open access
- green
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- CoChat. (2026). Citation check: Enantioselective Construction of Spirocyclic Oxindolic Cyclopentanes by Palladium-Catalyzed Trimethylenemethane-[3+2]-Cycloaddition. https://app.cochat.ai/papers/10.1021/ja075335w
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- Trost, B. M., Cramer, N., & Silverman, S. M. (2007). Enantioselective Construction of Spirocyclic Oxindolic Cyclopentanes by Palladium-Catalyzed Trimethylenemethane-[3+2]-Cycloaddition. Journal of the American Chemical Society. https://doi.org/10.1021/ja075335w
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