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Synthesis
DOI: 10.1055/a-2580-8900
paper

The Asymmetric Synthesis of CF3-Containing Spiro[indoline-3,2'-pyrrolidine] s via Organocatalytic Cycloaddition

Yisheng Cao
1   School of Basic Medical Sciences, The Institute of Pharmacology, LANZHOU, China
,
Zhiqiang Shen
1   School of Basic Medical Sciences, The Institute of Pharmacology, LANZHOU, China
,
jingke zhang
2   lanzhou university, Lanzhou University Laboratory Center for Medical Sciences, Lanzhou, China (Ringgold ID: RIN628944)
,
Haotian Chen
1   School of Basic Medical Sciences, The Institute of Pharmacology, LANZHOU, China
,
Wenbo Zhu
1   School of Basic Medical Sciences, The Institute of Pharmacology, LANZHOU, China
,
Jian Han
1   School of Basic Medical Sciences, The Institute of Pharmacology, LANZHOU, China
,
Wenjin Yan
1   School of Basic Medical Sciences, The Institute of Pharmacology, LANZHOU, China
› Author AffiliationsSupported by: Basic and Applied Basic Research Foundation of Guangdong Province 2022A1515220122
Supported by: National Natural Science Foundation of China 82270143 and 81660126
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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 through a chiral guanidine catalized [3+2] cycloaddition reaction. The mild reaction condition, low catalyst loading and high reaction rate make this synthetic method highly attractive for pharmaceutical synthesis.



Publication History

Received: 15 January 2025

Accepted after revision: 10 April 2025

Accepted Manuscript online:
10 April 2025

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