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Access to P ‐ and Axially Chiral Biaryl Phosphine Oxides by Enantioselective Cp x Ir III ‐Catalyzed C−H Arylations
Author(s) -
Jang YunSuk,
Woźniak Łukasz,
Pedroni Julia,
Cramer Nicolai
Publication year - 2018
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201807749
Subject(s) - enantioselective synthesis , phosphine , chemistry , cyclopentadienyl complex , catalysis , steric effects , iridium , denticity , ligand (biochemistry) , medicinal chemistry , stereochemistry , combinatorial chemistry , organic chemistry , crystal structure , biochemistry , receptor
An enantioselective C−H arylation of phosphine oxides with o ‐quinone diazides catalyzed by an iridium(III) complex bearing an atropchiral cyclopentadienyl (Cp x ) 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.