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Asymmetric Two-Component Alkenyl Catellani Reaction for the Construction of C--N Axial Chirality.
- Source :
- Chinese Journal of Chemistry; Apr2024, Vol. 42 Issue 7, p699-704, 6p
- Publication Year :
- 2024
-
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]
Details
- Language :
- English
- ISSN :
- 1001604X
- Volume :
- 42
- Issue :
- 7
- Database :
- Complementary Index
- Journal :
- Chinese Journal of Chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 176825277
- Full Text :
- https://doi.org/10.1002/cjoc.202300621