Third-Generation Amino Acid Furanoside-Based Ligands from d -Mannose for the Asymmetric Transfer Hydrogenation of Ketones: Catalysts with an Exceptionally Wide Substrate Scope

2016 ◽  
Vol 358 (24) ◽  
pp. 4006-4018 ◽  
Author(s):  
Jèssica Margalef ◽  
Tove Slagbrand ◽  
Fredrik Tinnis ◽  
Hans Adolfsson ◽  
Montserrat Diéguez ◽  
...  
Keyword(s):  
Amino Acid ◽  
Transfer Hydrogenation ◽  
Third Generation ◽  
Asymmetric Transfer Hydrogenation

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

Catalysts ◽  
2021 ◽  
Vol 11 (6) ◽  
pp. 671
Author(s):  
Chad M. Bernier ◽  
Joseph S. Merola
Keyword(s):  
Amino Acids ◽  
Amino Acid ◽  
Enantiomeric Excess ◽  
Transfer Hydrogenation ◽  
Acid Catalysts ◽  
Asymmetric Transfer Hydrogenation ◽  
Reaction Conditions ◽  
Chiral Complexes ◽  
Acetophenone Derivatives ◽  
Aryl Ketones

A series of chiral complexes of the form Ir(NHC)2(aa)(H)(X) (NHC = N-heterocyclic carbene, aa = chelated amino acid, X = halide) was synthesized by oxidative addition of -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)2(l-Pro)(H)(I) catalyst (IMe = 1,3-dimethylimidazol-2-ylidene), which asymmetrically reduces a range of acetophenone derivatives in up to 95% enantiomeric excess.

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