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Highly Enantioselective [3+2] Annulation of Morita–Baylis–Hillman Adducts Mediated by L‐Threonine‐Derived Phosphines: Synthesis of 3‐Spirocyclopentene‐2‐oxindoles having Two Contiguous Quaternary Centers
Open accessAbstract
Spiral bound: The Morita–Baylis–Hillman adducts were employed as C3 synthons in the asymmetric [3+2] annulation with malonitrile substrates using L-threonine-derived 1 as the catalyst (see scheme). The reaction is highly regioselective and stereoselective, and affords optically enriched 3-spirocyclopentene-2-oxindoles containing two contiguous quaternary centers. Boc=tert-butoxycarbonyl, PMB=para-methoxybenzyl, TIPS=triisopropylsilyl.
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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
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
- Zhong, F., Han, X., Wang, Y., & Lu, Y.
- Venue
- Angewandte Chemie International Edition
- Publisher
- Wiley
- Published
- 2011-07-04
- Volume
- 50
- Issue
- 34
- Pages
- 7837-7841
- ISSN
- 1433-7851 (ISSN-L)
- 1521-3773
- OpenAlex
- W2066216620
- Cited by
- 419
- References
- 1
- FWCI
- 27.68
- Type
- journal article
- Language
- en
- Open access
- bronze
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- CoChat. (2026). Citation check: Highly Enantioselective [3+2] Annulation of Morita–Baylis–Hillman Adducts Mediated by L‐Threonine‐Derived Phosphines: Synthesis of 3‐Spirocyclopentene‐2‐oxindoles having Two Contiguous Quaternary Centers. https://app.cochat.ai/papers/10.1002/anie.201102094
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- Zhong, F., Han, X., Wang, Y., & Lu, Y. (2011). Highly Enantioselective [3+2] Annulation of Morita–Baylis–Hillman Adducts Mediated by L‐Threonine‐Derived Phosphines: Synthesis of 3‐Spirocyclopentene‐2‐oxindoles having Two Contiguous Quaternary Centers. Angewandte Chemie International Edition. https://doi.org/10.1002/anie.201102094
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