Catalytic asymmetric synthesis of spirooxindoles: recent developments
Abstract
Chiral spirooxindoles are privileged heterocyclic motifs, which are widely found in natural alkaloids and pharmaceuticals. Moreover, the construction of chiral spiro-cyclic frameworks is a long-lasting challenge in organic synthesis. The past four years have witnessed significant developments in this field, and this feature article outlines the recent progress in the catalytic asymmetric synthesis of spirooxindoles, including the contributions of our group. The catalytic asymmetric construction of spirooxindoles has greatly benefited from the utilization of oxindole derivatives as starting materials, including isatin derivatives, methyleneindolinones, indolin-2-one derivatives and isatin-derived 3-indolylmethanols. This article is divided into sections according to the size and type of the generated spiro-ring fused at the C3-position of the oxindole core (from three-membered to seven-membered spiro-rings), and representative examples are given with illustrations. In addition, the enantioselective construction of bispirooxindole frameworks is also discussed in the last section.
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THN-fused C3-spirooxindoles should possess good druglikeness because THN and spirooxindole derivatives are privileged drug-like architectures.
“We started with THN54, 55, 56, 57, 58, 59, 60, 61 and spirooxindole derivatives62, 63, 64, 65, 66, 67, 68, 69, 70, 71, 72 because they are privileged drug-like architectures, so the resulting THN-fused C3-spirooxindoles should possess good druglikeness (Fig. 2C).”
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Flagged first, then by citations
Cited by
Sorted by citations
Wang, B., Peng, F., Huang, W., Zhou, J., Zhang, N., Sheng, J., Haruehanroengra, P., He, G., & Han, B. (2020) · Acta Pharmaceutica Sinica B · doi:10.1016/j.apsb.2019.12.013 · Cited by 73 · see citing works
- Authors
- Mei, G.-J., & Shi, F.
- Affiliations
- Jiangsu Normal University (CN)
- Corresponding author
- Shi, Feng
- Venue
- Chemical Communications
- Publisher
- Royal Society of Chemistry (RSC)
- Published
- 2018
- Volume
- 54
- Issue
- 50
- Pages
- 6607-6621
- ISSN
- 1359-7345 (ISSN-L)
- 1364-548X
- OpenAlex
- W2800447397
- Cited by
- 467
- References
- 214
- Citations by year
- 2026: 29 · 2025: 45 · 2024: 49 · 2023: 41 · 2022: 56 · 2021: 88 · 2020: 57 · 2019: 83 · 2018: 19
- FWCI
- 25.30
- Type
- journal article
- Language
- en
- Open access
- closed
- Locations
- Chemical Communications (publishedVersion)
- PubMed (publishedVersion)
- Funders
- National Natural Science Foundation of China (21772069, 21702077)
- Natural Science Foundation of Jiangsu Province (BK20160003 and BK20170227)
- Topics
- Physical Sciences › Chemistry › Organic Chemistry › Asymmetric Synthesis and Catalysis
- Physical Sciences › Chemistry › Organic Chemistry › Synthesis of Indole Derivatives
- Physical Sciences › Chemistry › Organic Chemistry › Axial and Atropisomeric Chirality Synthesis
- Keywords
- asymmetric catalysis, spirooxindoles, oxindole derivatives, isatin derivatives, methyleneindolinones, indolin-2-one derivatives, asymmetric synthesis, heterocyclic synthesis
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