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

• Published in: Nature communications Vol. 14; no. 1; p. 3380
• Main Authors: Li, Chengwen, Shao, Ying-Bo, Gao, Xi, Ren, Zhiyuan, Guo, Chenhao, Li, Meng, Li, Xin
• Format: Journal Article
• Language: English
• Published: London Nature Publishing Group UK 08.06.2023; Nature Publishing Group; Nature Portfolio
• Subjects: 119/118; 639/301/923/3931; 639/638/298/398; 639/638/403/935; Acids; Catalysis; Chemical synthesis; Electrochemical analysis; Electrochemistry; Enantiomers; Humanities and Social Sciences; Laboratories; Materials science; multidisciplinary; Phosphoric acid; Photochemicals; Science; Science (multidisciplinary); Substrates
• ISSN: 2041-1723; 2041-1723
• DOI: 10.1038/s41467-023-39134-9

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. Heterohelicenes are of increasing importance in materials science but organocatalytic enantioselective synthesis of these molecules remains challenging. Here, the authors synthesize enantioenriched 1-(3-indol)-quino[n]helicenes through chiral phosphoric acid-catalyzed Povarov reaction followed by oxidative aromatization and explore the photochemical and electrochemical properties of these compounds.