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Access to P- and Axially Chiral Biaryl Phosphine Oxides by Enantioselective Cpx IrIII -Catalyzed C-H Arylations.

Yun-Suk JangŁukasz WoźniakJulia PedroniNicolai Cramer
Published in: Angewandte Chemie (International ed. in English) (2018)
An enantioselective C-H arylation of phosphine oxides with o-quinone diazides catalyzed by an iridium(III) complex bearing an atropchiral cyclopentadienyl (Cpx ) ligand and phthaloyl tert-leucine as co-catalyst is reported. The method allows access to a) P-chiral biaryl phosphine oxides, b) atropo-enantioselective construction of sterically demanding biaryl backbones, and also c) selective assembly of axial and P-chiral compounds in excellent yields and diastereo- and enantioselectivities. Enantiospecific reductions provide monodentate chiral phosphorus(III) compounds having structures and biaryl backbones with proven importance as ligands in asymmetric catalysis.
Keyphrases
  • ionic liquid
  • room temperature
  • capillary electrophoresis
  • visible light