title: Synthesis of axially chiral biaryls through sulfoxide-directed asymmetric mild C-H activation and dynamic kinetic resolution.
abstract: A mild and robust direct C-H functionalization strategy has been applied to the synthesis of axially chiral biaryls. Such an efficient and stereoselective transformation occurs through an original dynamic kinetic resolution pathway enabling the conversion of diastereomeric mixtures of non-prefunctionalized substrates into atropisomerically pure, highly substituted biaryl scaffolds. The main feature of this transformation is the use of an enantiopure sulfoxide as both chiral auxiliary and traceless directing group. The potential of newly synthesized biaryls as valuable building blocks is further illustrated.
authors.affiliation: Laboratoire de Chimie Moléculaire (UMR CNRS 7509), Université de Strasbourg, ECPM, 25 Rue Becquerel, 67087, Strasbourg (France).
authors.forename: Chinmoy Kumar
authors.initials: CK
authors.lastname: Hazra
authors.forename: Quentin
authors.initials: Q
authors.lastname: Dherbassy
authors.forename: Joanna
authors.initials: J
authors.lastname: Wencel-Delord
authors.forename: Françoise
authors.initials: F
authors.lastname: Colobert
mesh_terms: D002244:Carbon / Q000737:chemistry*; D006859:Hydrogen / Q000737:chemistry*; D007700:Kinetics; D013237:Stereoisomerism; D013454:Sulfoxides / Q000737:chemistry*
chemical_list: D013454:Sulfoxides; D002244:Carbon; D006859:Hydrogen
keywords: CH activation; asymmetric synthesis; atroposelectivity; dynamic kinetic resolution; sulfoxides