Enantioselective Synthesis of Biaryl Atropisomers by Pd‐Catalyzed C−H Olefination using Chiral Spiro Phosphoric Acid Ligands

The discovery of proper ligands to simultaneously modulate the reactivity and effectively control the stereoselectivity is a central topic in the field of enantioselective C−H activation. Herein, we reported the synthesis of axially chiral biaryls by Pd‐catalyzed atroposelective C−H olefination. A n...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2019-05, Vol.58 (20), p.6708-6712
Main Authors: Luo, Jun, Zhang, Tao, Wang, Lei, Liao, Gang, Yao, Qi‐Jun, Wu, Yong‐Jie, Zhan, Bei‐Bei, Lan, Yu, Lin, Xu‐Feng, Shi, Bing‐Feng
Format: Article
Language:English
Subjects:
atroposelectivity
Chemical synthesis
chiral spiro phosphoric acids
C−H olefination
Density functional theory
Enantiomers
Ligands
Palladium
Phosphoric acid
Quinoline
quinoline biaryls
Stereoselectivity
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Summary:The discovery of proper ligands to simultaneously modulate the reactivity and effectively control the stereoselectivity is a central topic in the field of enantioselective C−H activation. Herein, we reported the synthesis of axially chiral biaryls by Pd‐catalyzed atroposelective C−H olefination. A novel chiral spiro phosphoric acid, STRIP, was identified as a superior ligand for this transformation. A broad range of axially chiral quinoline derivatives were synthesized in good yields with excellent enantioselectivities (up to 98 % ee). Density functional theory was used to gain a theoretical understanding of the enantioselectivities in this reaction. The discovery of proper ligands to simultaneously modulate the reactivity and effectively control the stereoselectivity is a central topic in the field of enantioselective C−H activation. Herein, the synthesis of axially chiral biaryls by Pd‐catalyzed atroposelective C−H olefination is reported. A broad range of axially chiral quinoline derivatives were synthesized in good yields with excellent enantioselectivities (up to 98 % ee).
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201902126