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Journal Articles Chemistry - A European Journal Year : 2022

Helical chiral N‐heterocyclic carbene ligands in enantioselective gold catalysis

Abstract

The first chiral helicene-NHC gold(I) complexes efficient in enantioselective catalysis were prepared. The L-shaped chiral ligand is composed of an imidazo[1,5-a]pyridin-3-ylidene (IPy) scaffold laterally-substituted by a configurationally stable [5]-helicenoid unit. The chiral information was introduced in a key post-functionalization step of a NHC-gold(I) complex bearing a symmetrical anionic fluoreno[5]helicene substituent, leading to a racemic mixture of complexes featuring three correlated elements of chirality, namely central, axial and helical chirality. After HPLC enantiomeric resolution, X-ray crystallography and theoretical calculations enabled structural and stereochemical characterization of these configurationally stable NHC-gold(I) complexes. The high potential in asymmetric catalysis is demonstrated in the benchmark cycloisomerization of N-tethered 1,6-enynes with up to 95:5 er.
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Dates and versions

hal-03575284 , version 1 (15-02-2022)

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Lenka Pallova, Laura Abella, Marion Jean, Nicolas Vanthuyne, Cécile Barthes, et al.. Helical chiral N‐heterocyclic carbene ligands in enantioselective gold catalysis. Chemistry - A European Journal, 2022, 28 (17), pp.e202200166. ⟨10.1002/chem.202200166⟩. ⟨hal-03575284⟩
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