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Palladium‐Catalyzed Asymmetric Construction of Vicinal All‐Carbon Quaternary Stereocenters and its Application to the Synthesis of Cyclotryptamine Alkaloids
Open accessAbstract
A twofold Pd-DAAA Pd-catalyzed decarboxylative allylic alkylation (see scheme) was used to construct two vicinal all-carbon quaternary stereocenters (marked in red) in a diastereo- and enantioselective fashion. The products of the Pd-DAAA were further elaborated to complete the formal syntheses of cyclotryptamine alkaloids. The twofold Pd-catalyzed transformation proceeds through an initial matched allylation followed by a second mismatched allylation to deliver the desired product.
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Citations
Cited by
All-carbon quaternary centers in natural products and medicinal chemistry: recent advances
Ling, T., & Rivas, F. (2016) · Tetrahedron · doi:10.1016/j.tet.2016.09.002 · Cited by 312
Recent advances in cooperative bimetallic asymmetric catalysis: dinuclear Schiff base complexes
Matsunaga, S., & Shibasaki, M. (2014) · Chem. Commun. · doi:10.1039/c3cc47587e · Cited by 263
Dalpozzo, R. (2017) · Advanced Synthesis & Catalysis · doi:10.1002/adsc.201700361 · Cited by 146
Metadata
- Authors
- Trost, B. M., & Osipov, M.
- Venue
- Angewandte Chemie International Edition
- Publisher
- Wiley
- Published
- 2013-07-03
- Volume
- 52
- Issue
- 35
- Pages
- 9176-9181
- ISSN
- 1433-7851 (ISSN-L)
- 1521-3773
- OpenAlex
- W2102790079
- Cited by
- 159
- References
- 0
- FWCI
- 9.49
- Type
- journal article
- Language
- en
- Open access
- green
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- CoChat. (2026). Citation check: Palladium‐Catalyzed Asymmetric Construction of Vicinal All‐Carbon Quaternary Stereocenters and its Application to the Synthesis of Cyclotryptamine Alkaloids. https://app.cochat.ai/papers/10.1002/anie.201302805
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- Trost, B. M., & Osipov, M. (2013). Palladium‐Catalyzed Asymmetric Construction of Vicinal All‐Carbon Quaternary Stereocenters and its Application to the Synthesis of Cyclotryptamine Alkaloids. Angewandte Chemie International Edition. https://doi.org/10.1002/anie.201302805
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