Enantioselective synthesis of chiral quinohelicenes through sequential organocatalyzed Povarov reaction and oxidative aromatization

Chengwen Li, Ying-Bo Shao, Xi Gao, Zhiyuan Ren, Chenhao Guo, Meng Li and Xin Li ()
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Chengwen Li: Nankai University
Ying-Bo Shao: Nankai University
Xi Gao: Nankai University
Zhiyuan Ren: Nankai University
Chenhao Guo: Chinese Academy of Sciences
Meng Li: Chinese Academy of Sciences
Xin Li: Nankai University

Nature Communications, 2023, vol. 14, issue 1, 1-9

Abstract: Abstract Heterohelicenes are of increasing importance in the fields of materials science, molecular recognition, and asymmetric catalysis. However, enantioselective construction of these molecules, especially by organocatalytic methods, is challenging, and few methods are available. In this study, we synthesize enantioenriched 1-(3-indol)-quino[n]helicenes through chiral phosphoric acid-catalyzed Povarov reaction followed by oxidative aromatization. The method has a broad substrate scope and offers rapid access to an array of chiral quinohelicenes with enantioselectivities up to 99%. Additionally, the photochemical and electrochemical properties of selected quinohelicenes are explored.

Date: 2023
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DOI: 10.1038/s41467-023-39134-9

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