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Discovery and Enantioselective Synthesis of Tetra-Substituted Methylene Oxindole Atropisomers by Palladium-Catalyzed Domino Cyclization

delete2024-09-04
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PRE
AI
M
Mei An
C
Chuan‐Jun Lu
F
Fang‐Bei Ge
周文光 (Wenguang Zhou)
L
Li‐Wen Zhan
张述伟 (Shuwei Zhang)
R
Renrong Liu *
DOI:10.1021/acscatal.4c04455delete
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Abstract

Abstract

En 中文
The discovery of atropisomers with unique skeletal structures is important for the development of chiral catalysts, ligands, drugs, and materials. Herein, we report the development of palladium-catalyzed enantioselective domino cyclization chemistry for generating tetra-substituted methylene oxindole atropisomers. A set of rarely reported oxindole-indole atropisomers was synthesized in high yields, with (Z)-stereoselectivities and good enantioselectivities under mild reaction conditions. Importantly, the formed oxindole-indole atropisomer motif could be transferred between Z- and E-alkenes that interconverts four different isomeric states in a fixed sequence upon light irradiation.
Keywords:
atropisomeric
palladium
oxindole
enantioselective
domino cyclization

Journal

ACS Catalysis cover
ACS Catalysis
IF:
13.1
Papers:
1.6W
Citations:
15.0W

Organization

Q
Qingdao University
Scholars:
3.1W
Papers: 2.1W
Citations: 3.7W
Y
Yangzhou University
Scholars:
2.8W
Papers: 1.9W
Citations: 3.3W