Atroposelective Synthesis of Axially Chiral C2-Arylindoles via Rhodium-Catalyzed Asymmetric C–H Bond Insertion
Junheng Liu, Qiongya Li, Ying Shao, Jiangtao Sun
Abstract
A highly efficient rhodium-catalyzed formal C–H insertion reaction between indoles and 1-diazonaphthoquinones has been established, providing a novel protocol for the atroposelective synthesis of axially chiral C2-arylindoles (up to 99:1 er) under mild reaction conditions. Typically, only 1 mol % of Rh2(S-PTTL)4 is used and the chelation group is not needed for this conversion.
Topics & Concepts
ChemistryRhodiumAxial symmetryCatalysisCombinatorial chemistryChelationMedicinal chemistryStereochemistryOrganic chemistryStructural engineeringEngineeringAxial and Atropisomeric Chirality SynthesisSphingolipid Metabolism and SignalingMolecular spectroscopy and chirality