Review
Chiral Cyclopentadienyl Ligands: Design, Syntheses, and Applications in Asymmetric Catalysis
Dr. Josep Mas-Roselló,
Dr. Ana G. Herraiz,
Benoît Audic,
Aragorn Laverny,
Prof. Dr. Nicolai Cramer,
Dr. Josep Mas-Roselló
Laboratory of Asymmetric Catalysis and Synthesis, Institute of Chemical Sciences and Engineering, Ecole Polytechnique Fédérale de Lausanne (EPFL), Lausanne, Switzerland
Search for more papers by this authorDr. Ana G. Herraiz
Laboratory of Asymmetric Catalysis and Synthesis, Institute of Chemical Sciences and Engineering, Ecole Polytechnique Fédérale de Lausanne (EPFL), Lausanne, Switzerland
These authors contributed equally to this work.
Search for more papers by this authorBenoît Audic
Laboratory of Asymmetric Catalysis and Synthesis, Institute of Chemical Sciences and Engineering, Ecole Polytechnique Fédérale de Lausanne (EPFL), Lausanne, Switzerland
These authors contributed equally to this work.
Search for more papers by this authorAragorn Laverny
Laboratory of Asymmetric Catalysis and Synthesis, Institute of Chemical Sciences and Engineering, Ecole Polytechnique Fédérale de Lausanne (EPFL), Lausanne, Switzerland
Search for more papers by this authorCorresponding Author
Prof. Dr. Nicolai Cramer
Laboratory of Asymmetric Catalysis and Synthesis, Institute of Chemical Sciences and Engineering, Ecole Polytechnique Fédérale de Lausanne (EPFL), Lausanne, Switzerland
Search for more papers by this authorDr. Josep Mas-Roselló,
Dr. Ana G. Herraiz,
Benoît Audic,
Aragorn Laverny,
Prof. Dr. Nicolai Cramer,
Dr. Josep Mas-Roselló
Laboratory of Asymmetric Catalysis and Synthesis, Institute of Chemical Sciences and Engineering, Ecole Polytechnique Fédérale de Lausanne (EPFL), Lausanne, Switzerland
Search for more papers by this authorDr. Ana G. Herraiz
Laboratory of Asymmetric Catalysis and Synthesis, Institute of Chemical Sciences and Engineering, Ecole Polytechnique Fédérale de Lausanne (EPFL), Lausanne, Switzerland
These authors contributed equally to this work.
Search for more papers by this authorBenoît Audic
Laboratory of Asymmetric Catalysis and Synthesis, Institute of Chemical Sciences and Engineering, Ecole Polytechnique Fédérale de Lausanne (EPFL), Lausanne, Switzerland
These authors contributed equally to this work.
Search for more papers by this authorAragorn Laverny
Laboratory of Asymmetric Catalysis and Synthesis, Institute of Chemical Sciences and Engineering, Ecole Polytechnique Fédérale de Lausanne (EPFL), Lausanne, Switzerland
Search for more papers by this authorCorresponding Author
Prof. Dr. Nicolai Cramer
Laboratory of Asymmetric Catalysis and Synthesis, Institute of Chemical Sciences and Engineering, Ecole Polytechnique Fédérale de Lausanne (EPFL), Lausanne, Switzerland
Search for more papers by this authorGraphical Abstract
Chiral cyclopentadienyls (CpX) have emerged as powerful steering ligands in asymmetric catalysis. This Review discusses the existing ligand classes, their design, syntheses, and metalation methods. Details on the successful application of the metal complexes in numerous catalytic processes are provided. Those include C−H bond functionalization chemistry and beyond, enabling access to valuable chiral molecules.
Abstract
The creation of new chiral ligands capable of providing high stereocontrol in metal-catalyzed reactions is crucial in modern organic synthesis. The production of bioactive molecules as single enantiomers is increasingly required, and asymmetric catalysis with metal complexes constitutes one of the most efficient synthetic strategies to access optically active compounds. Herein we offer a historical overview on the development of chiral derivatives of the ubiquitous cyclopentadienyl ligand (CpX), and detail their successful application in a broad range of metal-catalyzed transformations. Those include the functionalization of challenging C−H bonds and beyond, giving access to an extensive catalogue of valuable chiral molecules. A critical comparison of the existing ligand families, their design, synthesis, and complexation to different metals is also provided. In addition, future research directions are discussed to further enhance the performance and application of CpX ligands in enantioselective catalysis.
Conflict of interest
The authors declare no conflict of interest.
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