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Enantioselective Synthesis of N-N Biaryl Atropisomers through Iridium(I)-Catalyzed C-H Alkylation with Acrylates.

Si-Yong YinQiansujia ZhouChen-Xu LiuQing GuShu-Li You
Published in: Angewandte Chemie (International ed. in English) (2023)
Enantioselective synthesis of N-N biaryl atropisomers is an emerging area but remains underexplored. The development of efficient synthesis of N-N biaryl atropisomers is in great demand. Herein, the construction of N-N biaryl atropisomers through iridium-catalyzed asymmetric C-H alkylation is reported for the first time. In the presence of readily available Ir precursor and Xyl-BINAP, a variety of axially chiral molecules based on indole-pyrrole skeleton were obtained in good yields (up to 98 %) with excellent enantioselectivity (up to 99 % ee). In addition, N-N bispyrrole atropisomers could also be synthesized in excellent yields and enantioselectivity. This method features perfect atom economy, wide substrate scope, and multifunctionalized products allowing diverse transformations.
Keyphrases
  • room temperature
  • ionic liquid
  • mass spectrometry