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Organocatalytic Direct Asymmetric Aldol Reactions of 3-Isothiocyanato Oxindoles to Ketones: Stereocontrolled Synthesis of Spirooxindoles Bearing Highly Congested Contiguous Tetrasubstituted Stereocenters
Abstract
The first example of a direct catalytic asymmetric intermolecular aldol reaction of 3-isothiocyanato oxindoles to simple ketones with bifunctional thiourea-tertiary amine as catalyst is reported. This strategy provides a promising approach for the asymmetric synthesis of a range of enantioenriched spirocyclic oxindoles bearing two highly congested contiguous tetrasubstituted carbon stereocenters. Versatile transformations of the spirocyclic oxindole products into other structurally diverse spirocyclic oxindoles have also been demonstrated.
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Citations
Cited by
Recent Advances in Asymmetric Organocatalytic Construction of 3,3′‐Spirocyclic Oxindoles
Hong, L., & Wang, R. (2013) · Advanced Synthesis & Catalysis · doi:10.1002/adsc.201200808 · Cited by 718
Catalytic asymmetric synthesis of spirooxindoles: recent developments
Mei, G.-J., & Shi, F. (2018) · Chemical Communications · doi:10.1039/c8cc02364f · Cited by 467
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
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
Metadata
- Authors
- Chen, W.-B., Wu, Z.-J., Hu, J., Cun, L.-F., Zhang, X.-M., & Yuan, W.-C.
- Venue
- Organic Letters
- Publisher
- American Chemical Society (ACS)
- Published
- 2011-04-07
- Volume
- 13
- Issue
- 9
- Pages
- 2472-2475
- ISSN
- 1523-7052 (ISSN-L)
- 1523-7060
- OpenAlex
- W2029136259
- Cited by
- 195
- References
- 0
- FWCI
- 14.36
- Type
- journal article
- Language
- en
- Open access
- closed
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- CoChat. (2026). Citation check: Organocatalytic Direct Asymmetric Aldol Reactions of 3-Isothiocyanato Oxindoles to Ketones: Stereocontrolled Synthesis of Spirooxindoles Bearing Highly Congested Contiguous Tetrasubstituted Stereocenters. https://app.cochat.ai/papers/10.1021/ol200724q
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- Chen, W.-B., Wu, Z.-J., Hu, J., Cun, L.-F., Zhang, X.-M., & Yuan, W.-C. (2011). Organocatalytic Direct Asymmetric Aldol Reactions of 3-Isothiocyanato Oxindoles to Ketones: Stereocontrolled Synthesis of Spirooxindoles Bearing Highly Congested Contiguous Tetrasubstituted Stereocenters. Organic Letters. https://doi.org/10.1021/ol200724q
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Contains information from the Semantic Scholar Academic Graph Datasets, made available under the ODC Attribution License (ODC-BY 1.0).
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