Hazra CK, Dherbassy Q, Wencel-Delord J, * Colobert F. * Université de Strasbourg, France
Synthesis of Axially Chiral Biaryls through Sulfoxide-Directed Asymmetric Mild C–H Activation and Dynamic Kinetic Resolution.
Angew. Chem. Int. Ed. 2014;
53: 13871-13875
Key words
palladium - chiral sulfoxides - atropisomers
Significance
Axially chiral biaryl motifs are privileged structures as ligands for transition-metal catalysis. The authors present a dynamic kinetic resolution of racemic biaryls with a palladium catalyst using point chirality of a sulfoxide directing group.
Comment
Although some substrates were slow to react (up to 7 days), good yields and stereoselectivities were observed. Treatment of the products with t-BuLi at –90 °C led to an axially stable aryllithium species, which was trapped with CO2.
