Access to P- and Axially Chiral Biaryl Phosphine Oxides by Enantioselective CpxIrIII-Catalyzed C−H Arylations
Yun-Suk Jang
Laboratory of Asymmetric Catalysis and Synthesis, EPFL SB ISIC LCSA, BCH 4305, CH-, 1015 Lausanne, Switzerland
Search for more papers by this authorDr. Łukasz Woźniak
Laboratory of Asymmetric Catalysis and Synthesis, EPFL SB ISIC LCSA, BCH 4305, CH-, 1015 Lausanne, Switzerland
Search for more papers by this authorDr. Julia Pedroni
Laboratory of Asymmetric Catalysis and Synthesis, EPFL SB ISIC LCSA, BCH 4305, CH-, 1015 Lausanne, Switzerland
Search for more papers by this authorCorresponding Author
Prof. Dr. Nicolai Cramer
Laboratory of Asymmetric Catalysis and Synthesis, EPFL SB ISIC LCSA, BCH 4305, CH-, 1015 Lausanne, Switzerland
Search for more papers by this authorYun-Suk Jang
Laboratory of Asymmetric Catalysis and Synthesis, EPFL SB ISIC LCSA, BCH 4305, CH-, 1015 Lausanne, Switzerland
Search for more papers by this authorDr. Łukasz Woźniak
Laboratory of Asymmetric Catalysis and Synthesis, EPFL SB ISIC LCSA, BCH 4305, CH-, 1015 Lausanne, Switzerland
Search for more papers by this authorDr. Julia Pedroni
Laboratory of Asymmetric Catalysis and Synthesis, EPFL SB ISIC LCSA, BCH 4305, CH-, 1015 Lausanne, Switzerland
Search for more papers by this authorCorresponding Author
Prof. Dr. Nicolai Cramer
Laboratory of Asymmetric Catalysis and Synthesis, EPFL SB ISIC LCSA, BCH 4305, CH-, 1015 Lausanne, Switzerland
Search for more papers by this authorGraphical Abstract
An enantioselective C−H arylation of phosphine oxides with o-quinone diazides is catalyzed by a CpxIrIII complex and chiral carboxylic acid co-catalyst. It provides a unifying access to P-chiral phosphine oxides, atropo-enantioselective construction of sterically demanding biaryl backbones, and a selective assembly of axial and P-chiral compounds in excellent yields and diastereo- and enantioselectivities.
Abstract
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.
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