The non-precious metal copper-catalyzed enantioselective hydrosilylation of a vast array of aryl cycloalkyl ketones with different ring sizes was studied systematically for the first time (up to 99% enantiomeric excess). The results demonstrated that the steric size of cycloalkyl groups has a significant influence on the reaction outcomes. The first stereoselective formation of a selection of cyclohexyl heteroaryl alcohols of up to 97% enantiopurity was realized as well. Dramatic temperature effects on both the enantiopurity and the absolute configuration of the alcohol products were observed in the reduction of some cyclohexyl pyridyl ketones.
Organic & Biomolecular Chemistry
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