Cited by 467Asymmetric Synthesis and CatalysisSynthesis of Indole DerivativesAxial and Atropisomeric Chirality Synthesis

Catalytic asymmetric synthesis of spirooxindoles: recent developments

Mei, Guang-Jian, Shi, Feng·2018·Chemical Communications

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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Crossref · 10.1039/c8cc02364f

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Authors
Mei, G.-J., & Shi, F.
Affiliations
Jiangsu Normal University (CN)
Corresponding author
Shi, Feng
Venue
Chemical Communications
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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