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. 2025 Feb 25;31(12):e202403792.
doi: 10.1002/chem.202403792. Epub 2025 Feb 5.

Development of Chiral-At-Ruthenium Mesoionic Carbene Catalysts

Nemrud Demirel  1 , Paul Moths  1 , Xiulan Xie  1 , Sergei I Ivlev  1 , Eric Meggers  1
Affiliations

Development of Chiral-At-Ruthenium Mesoionic Carbene Catalysts

Nemrud Demirel et al. Chemistry. .

Abstract

Building on our previously established chiral-at-metal approach, in which the overall chirality of the transition metal catalyst is solely determined by a stereogenic metal center, we here present a new addition to the family of C2-symmetric chiral-at-ruthenium catalysts. These are C2-symmetric chiral ruthenium complexes featuring strongly σ-donating 1,2,3-triazol-5-ylidene mesoionic carbene (MIC) ligands. The complexes demonstrate excellent catalytic activity and enantioselectivity in a nitrene-mediated ring-closing C(sp3)-H amination of an aliphatic azide, leading to the formation of an N-Boc-protected chiral pyrrolidine. This study highlights the potential of this new class of chiral mesoionic carbene ruthenium complexes to further enhance or modify the reactivity of ruthenium-based chiral-at-metal catalysts.

Keywords: Asymmetric catalysis; Chiral-at-metal; Mesoionic carbenes; Metal-centered-chirality; Pyrrolidines; Ruthenium.

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References

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