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Enantioselective Synthesis of Pyridines with All‐Carbon Quaternary Carbon Centers via Cobalt‐Catalyzed Desymmetric [2+2+2] Cycloaddition
Author(s) -
Li Ke,
Wei Linsheng,
Sun Minghe,
Li Bing,
Liu Min,
Li Changkun
Publication year - 2021
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.202105452
Subject(s) - enantioselective synthesis , cycloaddition , regioselectivity , alkyl , chemistry , ligand (biochemistry) , catalysis , cobalt , carbon fibers , aryl , medicinal chemistry , silylation , organic chemistry , receptor , materials science , biochemistry , composite number , composite material
A Co‐catalyzed enantioselective desymmetric [2+2+2] cycloaddition for synthesis of pyridines with all‐carbon quaternary carbon centers has been developed. The regio‐ and enantioselectivities are controlled by the inherent nature of terminal alkynes and the substituents on the bisoxazolinephosphine ligands. Pyridines with 5‐substitutents could be obtained with >20:1 regioselectivity and up to 94 % ee when terminal alkyl, alkenyl or silyl alkynes and DTBM/Ph‐based NPN* ligand L6 were used. Terminal aryl alkynes and Ph/Bn‐based ligand L4 leads to formation of pyridines with 6‐substitutents in up to 99 % ee .