Access to P‐ and Axially Chiral Biaryl Phosphine Oxides by Enantioselective CpxIrIII‐Catalyzed C−H Arylations DOI

Yun‐Suk Jang,

Łukasz Woźniak, Julia Pedroni

et al.

Angewandte Chemie, Journal Year: 2018, Volume and Issue: 130(39), P. 13083 - 13087

Published: July 25, 2018

Abstract An enantioselective C−H arylation of phosphine oxides with o ‐quinone diazides catalyzed by an iridium(III) complex bearing atropchiral cyclopentadienyl (Cp x ) ligand and phthaloyl tert ‐leucine as co‐catalyst is reported. The method allows access to a) P ‐chiral biaryl oxides, b) atropo‐enantioselective construction sterically demanding backbones, also c) selective assembly axial compounds in excellent yields diastereo‐ enantioselectivities. Enantiospecific reductions provide monodentate chiral phosphorus(III) having structures backbones proven importance ligands asymmetric catalysis.

Language: Английский

Catalytic Enantioselective Methylene C(sp3)−H Amidation of 8‐Alkylquinolines Using a Cp*RhIII/Chiral Carboxylic Acid System DOI

Seiya Fukagawa,

M. Kojima, Tatsuhiko Yoshino

et al.

Angewandte Chemie International Edition, Journal Year: 2019, Volume and Issue: 58(50), P. 18154 - 18158

Published: Oct. 8, 2019

Catalytic enantioselective directed methylene C(sp3 )-H amidation reactions of 8-alkylquinolines using a Cp*RhIII /chiral carboxylic acid (CCA) hybrid catalytic system are described. A binaphthyl-based chiral efficiently differentiates between the enantiotopic C-H bonds, which leads to formation C-N bonds with good enantioselectivity.

Language: Английский

Citations

114
α-Branched amines by catalytic 1,1-addition of C–H bonds and aminating agents to terminal alkenes DOI
Soham Maity,

Tyler J. Potter,

Jonathan A. Ellman

et al.

Nature Catalysis, Journal Year: 2019, Volume and Issue: 2(9), P. 756 - 762

Published: Aug. 12, 2019

Language: Английский

Citations

113
Cobalt(III)‐Catalyzed Enantioselective Intermolecular Carboamination by C−H Functionalization DOI

Kristers Ozols,

Shunsuke Onodera,

Łukasz Woźniak

et al.

Angewandte Chemie International Edition, Journal Year: 2020, Volume and Issue: 60(2), P. 655 - 659

Published: Sept. 28, 2020

Abstract High‐valent cyclopentadienyl cobalt catalysis is a versatile tool for sustainable C−H bond functionalizations. To harness the full potential of this strategy, control stereoselectivity these processes necessary. Herein, we report highly enantioselective intermolecular carboaminations alkenes through activation N ‐phenoxyamides catalyzed by Co III ‐complexes equipped with chiral (Cp x ) ligands. The method converts widely available acrylates as well bicyclic olefins into attractive enantioenriched isotyrosine derivatives elaborated amino‐substituted scaffolds under very mild conditions. outlined reactivity unique to Cp complexes and complementary 4d‐ 5d‐ precious‐metal catalysts.

Language: Английский

Citations

110
Rhodium(III)‐Catalyzed Atroposelective Synthesis of Biaryls by C−H Activation and Intermolecular Coupling with Sterically Hindered Alkynes DOI
Fen Wang, Zisong Qi,

Yuxia Zhao

et al.

Angewandte Chemie International Edition, Journal Year: 2020, Volume and Issue: 59(32), P. 13288 - 13294

Published: April 16, 2020

Abstract Reported herein is the atroposelective synthesis of biaryl NH isoquinolones by Rh III ‐catalyzed C−H activation benzamides and intermolecular [4+2] annulation for a broad scope 2‐substituted 1‐alkynylnaphthalenes, as well sterically hindered, symmetric diarylacetylenes. The axial chirality constructed based on dynamic kinetic transformation alkyne in redox‐neutral with benzamides, insertion being stereodetermining. reaction accommodates both heteroaryl carboxamides proceeds excellent regioselectivity (if applicable) enantioselectivities (average 91.8 % ee ). An enantiomerically diastereomerically pure rhodacyclic complex was prepared offers insight into enantiomeric control coupling system, wherein steric interactions between amide directing group substrate dictate regio‐ enantioselectivity.

Language: Английский

Citations

109
Access to P‐ and Axially Chiral Biaryl Phosphine Oxides by Enantioselective CpxIrIII‐Catalyzed C−H Arylations DOI

Yun‐Suk Jang,

Łukasz Woźniak, Julia Pedroni

et al.

Angewandte Chemie, Journal Year: 2018, Volume and Issue: 130(39), P. 13083 - 13087

Published: July 25, 2018

Abstract An enantioselective C−H arylation of phosphine oxides with o ‐quinone diazides catalyzed by an iridium(III) complex bearing atropchiral cyclopentadienyl (Cp x ) ligand and phthaloyl tert ‐leucine as co‐catalyst is reported. The method allows access to a) P ‐chiral biaryl oxides, b) atropo‐enantioselective construction sterically demanding backbones, also c) selective assembly axial compounds in excellent yields diastereo‐ enantioselectivities. Enantiospecific reductions provide monodentate chiral phosphorus(III) having structures backbones proven importance ligands asymmetric catalysis.

Language: Английский

Citations

108