1. Asymmetric Two-Component Alkenyl Catellani Reaction for the Construction of C--N Axial Chirality.
- Author
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Chenggui Wu, Ze-Shui Liu, Yong Shang, Chang Liu, Shuang Deng, Hong-Gang Cheng, Hengjiang Cong, Yinchun Jiao, and Qianghui Zhou
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CHIRALITY element , *ARAMID fibers , *ARYL bromides , *AMIDES , *ATROPISOMERS , *ALLYLIC alkylation , *ASYMMETRIC synthesis , *AMIDASES - Abstract
Herein, we report an asymmetric two-component alkenyl Catellani reaction for the construction of C--N axial chirality through a palladium/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 originates 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 diastereocontrol. [ABSTRACT FROM AUTHOR]
- Published
- 2024
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