Recent Advances in Asymmetric Addition Reactions to Isatins

Ke Xie; Ao Li; Bao-Rui Kong; Zhi-Chao Chen; Wei Du; Ying-Chun Chen

doi:10.1055/a-2376-6463

Synthesis, Inhaltsverzeichnis

Synthesis 2025; 57(05): 937-952
DOI: 10.1055/a-2376-6463

short review

Recent Advances in Asymmetric Addition Reactions to Isatins

Ke Xie‡

^aKey Laboratory of Drug-Targeting and Drug Delivery System of the Education Ministry and Sichuan Province, and Sichuan Research Center for Drug Precision Industrial Technology, West China School of Pharmacy, Sichuan University, Chengdu 610041, P. R. of China

,

Ao Li‡

^aKey Laboratory of Drug-Targeting and Drug Delivery System of the Education Ministry and Sichuan Province, and Sichuan Research Center for Drug Precision Industrial Technology, West China School of Pharmacy, Sichuan University, Chengdu 610041, P. R. of China

,

Bao-Rui Kong

^aKey Laboratory of Drug-Targeting and Drug Delivery System of the Education Ministry and Sichuan Province, and Sichuan Research Center for Drug Precision Industrial Technology, West China School of Pharmacy, Sichuan University, Chengdu 610041, P. R. of China

,

Zhi-Chao Chen∗

^aKey Laboratory of Drug-Targeting and Drug Delivery System of the Education Ministry and Sichuan Province, and Sichuan Research Center for Drug Precision Industrial Technology, West China School of Pharmacy, Sichuan University, Chengdu 610041, P. R. of China

,

Wei Du

^aKey Laboratory of Drug-Targeting and Drug Delivery System of the Education Ministry and Sichuan Province, and Sichuan Research Center for Drug Precision Industrial Technology, West China School of Pharmacy, Sichuan University, Chengdu 610041, P. R. of China

,

Ying-Chun Chen ∗

^aKey Laboratory of Drug-Targeting and Drug Delivery System of the Education Ministry and Sichuan Province, and Sichuan Research Center for Drug Precision Industrial Technology, West China School of Pharmacy, Sichuan University, Chengdu 610041, P. R. of China

^bCollege of Pharmacy, Third Military Medical University, Chongqing 400038, P. R. of China

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Abstract

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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 catalysis

Volltext

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