Abstract
In this account, we describe the design, synthesis and applications of tethered versions of the Ru(II)/N-tosyl-1,2-diphenylethylene-1,2-diamine (TsDPEN) class of catalyst that are commonly used for asymmetric transfer hydrogenation and asymmetric hydrogenation of ketones and imines. The review covers key aspects of the reaction mechanisms and examples of applications, including industrial applications to pharmaceutically important target molecules. In addition, closely related catalysts based on Rh(III) and Ir(III) are also described.
Highlights
Introduction to Asymmetric Transfer HydrogenationThe asymmetric reduction of ketones and imines is a pivotal method for the synthesis of chiral alcohols and amines, respectively
In this account, we describe the design, synthesis and applications of tethered versions of the Ru(II)/N-tosyl-1,2-diphenylethylene-1,2-diamine (TsDPEN) class of catalyst that are commonly used for asymmetric transfer hydrogenation and asymmetric hydrogenation of ketones and imines
Used tethered catalyst 8 in the synthesis of a functionalised tetrahydroxanthone related to kigamicin A (Figure 26),[48] but the product ee was modest, superior to that obtained with the first-generation untethered catalyst
Summary
The asymmetric reduction of ketones and imines is a pivotal method for the synthesis of chiral alcohols and amines, respectively. CH/p) electrostatic interaction favours the positioning of the substrate aryl group adjacent to the h6-arene ring of the catalyst in the transition state This ensures that a predictable major enantiomer of product is formed.[8,13] it should be noted that a minor hydride is often observed during in situ studies of the reduction reactions.[14] This may be due to the formation of a less reactive minor diastereoisomer of the hydride. Marko in Belgium, working on catalysts for ethylene and propylene polymerisation, he joined ICI Synetix in 2001, later to become part of Johnson Matthey His core interest is in catalytic research and in the synthetic development of ligands and metal compounds with catalytic activity. His research interests lie in asymmetric catalysis and the development of novel synthetic methodology
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