Design of Iridium N-Heterocyclic Carbene Amino Acid Catalysts for Asymmetric Transfer Hydrogenation of Aryl Ketones

A series of chiral complexes of the form Ir(NHC)<sub>2</sub>(aa)(H)(X) (NHC = N-heterocyclic carbene, aa = chelated amino acid, X = halide) was synthesized by oxidative addition of α-amino acids to iridium(I) bis-NHC compounds and screened for asymmetric transfer hydrogenation of ketones...

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Bibliographic Details
Main Authors: Chad M. Bernier, Joseph S. Merola
Format: Article
Language:English
Published: MDPI AG 2021-05-01
Series:Catalysts
Subjects:
Online Access:https://www.mdpi.com/2073-4344/11/6/671
Description
Summary:A series of chiral complexes of the form Ir(NHC)<sub>2</sub>(aa)(H)(X) (NHC = N-heterocyclic carbene, aa = chelated amino acid, X = halide) was synthesized by oxidative addition of α-amino acids to iridium(I) bis-NHC compounds and screened for asymmetric transfer hydrogenation of ketones. Following optimization of the reaction conditions, NHC, and amino acid ligands, high enantioselectivity was achieved when employing the Ir(IMe)<sub>2</sub>(<span style="font-variant: small-caps;">l</span>-Pro)(H)(I) catalyst (IMe = 1,3-dimethylimidazol-2-ylidene), which asymmetrically reduces a range of acetophenone derivatives in up to 95% enantiomeric excess.
ISSN:2073-4344