Catalytic Atroposelective C7 Functionalisation of Indolines and Indoles

Axially chiral atropisomeric compounds are widely applied in asymmetric catalysis and medicinal chemistry. In particular, axially chiral indole- and indoline-based frameworks have been recognised as important heterobiaryl classes because they are the core units of bioactive natural alkaloids, chiral ligands and bioactive compounds. Among them, the synthesis of C7-substituted indole biaryls and the analogous indoline derivatives is particularly challenging, and methods for their efficient synthesis are in high demand. Transition-metal catalysis is considered one of the most efficient methods to construct atropisomers. Here, we report the enantioselective synthesis of C7-indolino- and C7-indolo biaryl atropisomers by means of C-H functionalisation catalysed by chiral RhJasCp complexes.

Automated summary

Axially chiral atropisomeric compounds, especially indole- and indoline-based frameworks, are important heterobiaryl classes widely applied in asymmetric catalysis and medicinal chemistry. The synthesis of C7-substituted indole biaryls and the analogous indoline derivatives is particularly challenging, and efficient methods for their synthesis are in high demand. Transition-metal catalysis is considered one of the most efficient methods for constructing atropisomers.