Abstract
Synthesis of 2-pyridyl oxazoline esters and their organocatalytic application to the enantioselective silane reduction of ketones.
Highlights
Asymmetric reductions of carbonyl and heterocarbonyl functional groups are fundamental organic transformations
Our group has an ongoing interest in the design and application of novel oxazoline based catalytic systems.[20,21,22]
A variety of functionalisation reactions would be carried out on the alcohol to give us various ligands with which we could study the effect of variations of functionality in the ligands 2-4 (Figure 2) on their catalytic performance, as organocatalysts in asymmetric catalytic reduction reactions
Summary
Asymmetric reductions of carbonyl and heterocarbonyl functional groups are fundamental organic transformations. Non stereoselective reduction of ketones and imines can be achieved with hydrides but the asymmetric reduction is a very active area of research[1] with new methods being reported regularly using a wide variety of reactions and reagents for example chiral ligand metal complexes in hydrogenation[2,3] and transfer hydrogenation,[4,5] enzymatic reduction[6] and chiral ligand metal complexes in hydrosilylation.[7,8]. These catalysts afforded good enantioselectivities in the hydrosilylation of both ketones (some in the 80-90% ee range) and imines (Some >80% ee), whereas other catalysts were more often designed to target only one of the reactions
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