Cooperative Effects between Chiral Cp x –Iridium(III) Catalysts and Chiral Carboxylic Acids in Enantioselective C−H Amidations of Phosphine Oxides | Zendy

Jang YunSuk | Zendy; Dieckmann Michael | Zendy; Cramer Nicolai | Zendy

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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.

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