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Synthesis 2025; 57(05): 937-952
DOI: 10.1055/a-2376-6463
DOI: 10.1055/a-2376-6463
short review
Recent Advances in Asymmetric Addition Reactions to Isatins
We are grateful for the financial support from the National Natural Science Foundation of China (NSFC; 92156005 and 21931006) and the Open Research Fund of State Key Laboratory of Southwestern Chinese Medicine Resources (SKLTCM2022018).
Abstract
The 3-substituted-3-hydroxy-2-oxindole scaffolds are not only widely encountered in bioactive compounds but also serve as versatile building blocks for the construction of diverse valuable architectures. Although numerous synthetic methodologies have been developed over the past decades, the asymmetric addition of nucleophiles or their equivalents to isatin substrates has proved to be one of the most efficient strategies for the synthesis of chiral 3-substituted-3-hydroxy-2-oxindoles. This Short Review aims to summarize the significant progress achieved in this field in recent years, with particular attention paid to reaction development, mechanism, and stereo-induction models.
1 Introduction
2 Asymmetric Alkylation of Isatins
3 Asymmetric Alkenylation and Dienylation of Isatins
4 Asymmetric Alkynylation of Isatins
5 Asymmetric Allenylation of Isatins
6 Asymmetric Arylation of Isatins
7 Asymmetric Annulations of Isatins
8 Conclusions and Outlooks
Key words
3-substituted-3-hydroxy-2-oxindole - isatin - asymmetric addition reaction - organocatalysis - metal catalysisPublication History
Received: 03 July 2024
Accepted after revision: 30 July 2024
Accepted Manuscript online:
30 July 2024
Article published online:
22 August 2024
© 2024. Thieme. All rights reserved
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