Asymmetric Synthesis of Trifluoromethyl-Containing Spiro[indoline-3,2′-pyrrolidine]s by Organocatalytic Cycloaddition

Yisheng Cao; Zhiqiang Shen; Jingke Zhang; Haotian Chen; Wenbo Zhu; Jian Han; Wenjin Yan

doi:10.1055/a-2580-8900

Synthesis, Table of Contents

Synthesis 2025; 57(14): 2221-2231
DOI: 10.1055/a-2580-8900

paper

Asymmetric Synthesis of Trifluoromethyl-Containing Spiro[indoline-3,2′-pyrrolidine]s by Organocatalytic Cycloaddition

Authors

Yisheng Cao‡

^aSchool of Basic Medical Sciences, Lanzhou University, Lanzhou 730000, P. R. of China
Zhiqiang Shen‡

^aSchool of Basic Medical Sciences, Lanzhou University, Lanzhou 730000, P. R. of China

^bLanzhou Institute of Chemical Physics, Chinese Academy of Sciences, Lanzhou Gansu, 730000, P. R. of China
Jingke Zhang

^cMedical Laboratory Center, Lanzhou University, Lanzhou 730000, P. R. of China
Haotian Chen

^aSchool of Basic Medical Sciences, Lanzhou University, Lanzhou 730000, P. R. of China
Wenbo Zhu

^aSchool of Basic Medical Sciences, Lanzhou University, Lanzhou 730000, P. R. of China
Jian Han∗

^aSchool of Basic Medical Sciences, Lanzhou University, Lanzhou 730000, P. R. of China
Wenjin Yan∗

^aSchool of Basic Medical Sciences, Lanzhou University, Lanzhou 730000, P. R. of China

Abstract

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Abstract

The unique biological activity of pyrrolidine compounds has attracted significant interest from medicinal chemists. This study presents a one-step synthesis of [indolyl-3,2′-pyrrolidine] compounds with three chiral centers and an α-CF₃ group in excellent yields and enantioselectivities by reacting trifluoroethyl ketoimine with unsaturated alkynyl ketone compounds by a chiral-guanidine-catalyzed [3+2] cycloaddition reaction. The mild reaction conditions, low catalyst loading, and high reaction rate make this synthetic method highly attractive for pharmaceutical synthesis.

Key words

asymmetric synthesis - trifluoromethyl-containing compounds - guanidine catalysis - spiropyrrolidines - [3+2] cycloaddition reaction

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References

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