Enantioselective synthesis of [4]helicenes by organocatalyzed intermolecular C-H amination

Xihong Liu (), Boyan Zhu, Xiaoyong Zhang, Hanwen Zhu, Jingying Zhang, Anqi Chu, Fujun Wang and Rui Wang ()
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Xihong Liu: Chinese Academy of Medical Sciences, 2019RU066, Lanzhou University
Boyan Zhu: Chinese Academy of Medical Sciences, 2019RU066, Lanzhou University
Xiaoyong Zhang: Shenzhen Bay Laboratory
Hanwen Zhu: Chinese Academy of Medical Sciences, 2019RU066, Lanzhou University
Jingying Zhang: Chinese Academy of Medical Sciences, 2019RU066, Lanzhou University
Anqi Chu: Chinese Academy of Medical Sciences, 2019RU066, Lanzhou University
Fujun Wang: Chinese Academy of Medical Sciences, 2019RU066, Lanzhou University
Rui Wang: Chinese Academy of Medical Sciences, 2019RU066, Lanzhou University

Nature Communications, 2024, vol. 15, issue 1, 1-12

Abstract: Abstract Catalytic asymmetric synthesis of helically chiral molecules has remained an outstanding challenge and witnessed fairly limited progress in the past decades. Current methods to construct such compounds almost entirely rely on catalytic enantiocontrolled fused-ring system extension. Herein, we report a direct terminal peri-functionalization strategy, which allows for efficient assembling of 1,12-disubstituted [4]carbohelicenes via an organocatalyzed enantioselective amination reaction of 2-hydroxybenzo[c]phenanthrene derivates with diazodicarboxamides. The key feature of this approach is that the stereochemical information of the catalyst could be transferred into not only the helix sense but also the remote C-N axial chirality of the products, thus enabling the synthesis of [4]- and [5]helicenes with both structural diversity and stereochemical complexity in good efficiency and excellent enantiocontrol. Besides, the large-scale preparations and representative transformations of the helical products further demonstrate the practicality of this protocol. Moreover, DFT calculations reveal that both the hydrogen bonds and the C-H---π interactions between the substrates and catalyst contribute to the ideal stereochemical control.

Date: 2024
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DOI: 10.1038/s41467-024-45049-w

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