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Cooperative Effects between Chiral Cp x –Iridium(III) Catalysts and Chiral Carboxylic Acids in Enantioselective C−H Amidations of Phosphine Oxides
Author(s) -
Jang YunSuk,
Dieckmann Michael,
Cramer Nicolai
Publication year - 2017
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201708440
Subject(s) - enantioselective synthesis , iridium , phosphine , cyclopentadienyl complex , enantiomer , ligand (biochemistry) , catalysis , chemistry , chiral ligand , medicinal chemistry , asymmetric hydrogenation , stereochemistry , organic chemistry , receptor , biochemistry
An enantioselective C−H amidation of phosphine oxides by using an iridium(III) catalyst bearing an atropchiral cyclopentadienyl (Cp x ) ligand is reported. A very strong cooperative effect between the chiral Cp x ligand and a phthaloyl tert‐leucine enabled the transformation. Matched–mismatched cases of the different acid enantiomers are shown. The amidated P‐chiral arylphosphine oxides are formed in yields of up to 95 % and with excellent enantioselectivities of up to 99:1 er. Enantiospecific reduction provides access to valuable P‐chiral phosphorus(III) compounds.