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  • Title: Enantioselective Synthesis of Biaryl Atropisomers by Pd-Catalyzed C-H Olefination using Chiral Spiro Phosphoric Acid Ligands.
    Author: Luo J, Zhang T, Wang L, Liao G, Yao QJ, Wu YJ, Zhan BB, Lan Y, Lin XF, Shi BF.
    Journal: Angew Chem Int Ed Engl; 2019 May 13; 58(20):6708-6712. PubMed ID: 30908779.
    Abstract:
    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.
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