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Organocatalytic Tandem Reaction to Construct Six‐Membered Spirocyclic Oxindoles with Multiple Chiral Centres through a Formal [2+2+2] Annulation
Abstract
An efficient tandem reaction for the asymmetric synthesis of six‐membered spirocyclic oxindoles has been successfully developed through a formal [2+2+2] annulation strategy. The amine‐catalysed stereoselective Michael addition of aliphatic aldehydes to electron‐deficient olefinic oxindole motifs gave chiral C3 components, which were further combined with diverse electrophiles (activated olefins or imines) to afford spirocyclic oxindoles with versatile molecular complexity (up to six contiguous stereogenic centres, high diastereo‐ and enantioselectivities).
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Ding, K., Lu, Y., Nikolovska-Coleska, Z., Wang, G., Qiu, S., Shangary, S., Gao, W., Qin, D., Stuckey, J., Krajewski, K., et al. (2006) · Journal of Medicinal Chemistry · doi:10.1021/jm051122a · Cited by 702
Structure-based design of potent non-peptide MDM2 inhibitors
Ding, K., Lu, Y., Nikolovska-Coleska, Z., Qiu, S., Ding, Y., Gao, W., Stuckey, J., Krajewski, K., Roller, P. P., Tomita, Y., et al. (2005) · Journal of the American Chemical Society · doi:10.1021/ja051147z · Cited by 657
Cited by
Recent advances in the synthesis of biologically active spirooxindoles
Santos, M. M. M. (2014) · Tetrahedron · doi:10.1016/j.tet.2014.08.005 · 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
- Jiang, K., Jia, Z., Chen, S., Wu, L., & Chen, Y.
- Venue
- Chemistry – A European Journal
- Publisher
- Wiley
- Published
- 2010-02-19
- Volume
- 16
- Issue
- 9
- Pages
- 2852-2856
- ISSN
- 0947-6539 (ISSN-L)
- 1521-3765
- OpenAlex
- W1964740544
- Cited by
- 236
- References
- 2
- FWCI
- 20.52
- Type
- journal article
- Language
- en
- Open access
- closed
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- Jiang, K., Jia, Z., Chen, S., Wu, L., & Chen, Y. (2010). Organocatalytic Tandem Reaction to Construct Six‐Membered Spirocyclic Oxindoles with Multiple Chiral Centres through a Formal [2+2+2] Annulation. Chemistry – A European Journal. https://doi.org/10.1002/chem.200903009
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Contains information from the Semantic Scholar Academic Graph Datasets, made available under the ODC Attribution License (ODC-BY 1.0).
Semantic Scholar’s data is described in: Kinney, R., et al. (2023). The Semantic Scholar Open Data Platform. arXiv:2301.10140.
