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Asymmetric Two-component Alkenyl Catellani Reaction for the Construction of C--N Axial Chirality
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  • Chengui Wu,
  • Ze-Shui Liu,
  • Yong Shang,
  • Chang Liu,
  • Shuang Deng,
  • Hong-Gang Cheng,
  • Hengjiang Cong,
  • Yinchun Jiao,
  • Qianghui Zhou
Chengui Wu
Anhui University of Chinese Medicine
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Ze-Shui Liu
Wuhan University
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Yong Shang
Wuhan University
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Chang Liu
Wuhan University
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Shuang Deng
Wuhan University
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Hong-Gang Cheng
Wuhan University
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Hengjiang Cong
Wuhan University
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Yinchun Jiao
Hunan University of Science and Technology
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Qianghui Zhou
Wuhan University

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Abstract

Herein we report an asymmetric two-component alkenyl Catellani reaction for the construction of C–N axial chirality through a pal-ladium/chiral norbornene cooperative catalysis and an axial-to-axial chirality transfer process. Various partially aromatic iodinated 2-pyridones, quinolones, coumarin and uracil substrates react with 2,6-disubstituted aryl bromides with a tethered amide group, to afford a wide variety of polycyclic C–N atropisomers (38 examples, up to 97% e.e.). The obtained C–N axial chirality is originated from the preformed transient C–C axial chirality with high fidelity. The synthetic utility of this chemistry is demonstrated by facile preparation of complex quinoline and pyridine based C–N atropisomers through a N-deprotection and aromatization sequence. In addition, a remote axial-to-central diastereoinduction process dictated by C–N axial chirality is observed with excellent diastere-ocontrol.
22 Nov 20231st Revision Received
22 Nov 2023Submission Checks Completed
22 Nov 2023Assigned to Editor
22 Nov 2023Review(s) Completed, Editorial Evaluation Pending
22 Nov 2023Editorial Decision: Accept