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ChiCAAC
Chiral Cyclic Alkyl Amino Carbenes in Asymmetric Catalysis
FunderFrench National Research Agency (ANR)
Funder Contribution €463,860.00
DurationFrom 01 Oct 2019
Project codeANR-19-CE07-0017
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Description
Following pioneering work by Bertrand in 1988, and the isolation of the first N-heterocyclic carbene (NHC) by Arduengo, the field of stable carbenes has witnessed outstanding breakthroughs and considerable developments. Due to their strong sigma-donating and pi-accepting character, and their simple, yet versatile synthesis, carbenes have successfully challenged the stronghold of phosphines in transition metal catalysis. In recent years, the success of achiral N-heterocyclic carbenes (NHCs) as stable electron-rich neutral ligands has triggered the development of a diversity of chiral NHCs as stereodirecting ancillary ligands for enantioselective transformations. Today, thanks to their modular design and the ease of accessing azolium salt precursors, tailor-made chiral NHCs have proven to be significant tools in asymmetric transformations. Despite these advances, the toolbox of available chiral carbenes still lags behind more classical chiral phosphine ligands. In part, this situation might originate from the seeming inability to capitalise on the rich structural and electronic diversity of stable singlet carbenes. The goal of this project is therefore to prepare new chiral carbene ligands (other than NHCs), in order to extend the still developing family of stable chiral carbenes.
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Following pioneering work by Bertrand in 1988, and the isolation of the first N-heterocyclic carbene (NHC) by Arduengo, the field of stable carbenes has witnessed outstanding breakthroughs and considerable developments. Due to their strong sigma-donating and pi-accepting character, and their simple, yet versatile synthesis, carbenes have successfully challenged the stronghold of phosphines in transition metal catalysis. In recent years, the success of achiral N-heterocyclic carbenes (NHCs) as stable electron-rich neutral ligands has triggered the development of a diversity of chiral NHCs as stereodirecting ancillary ligands for enantioselective transformations. Today, thanks to their modular design and the ease of accessing azolium salt precursors, tailor-made chiral NHCs have proven to be significant tools in asymmetric transformations. Despite these advances, the toolbox of available chiral carbenes still lags behind more classical chiral phosphine ligands. In part, this situation might originate from the seeming inability to capitalise on the rich structural and electronic diversity of stable singlet carbenes. The goal of this project is therefore to prepare new chiral carbene ligands (other than NHCs), in order to extend the still developing family of stable chiral carbenes.
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