Abstract
Enantioselective reductions of prochiral ferrocenophane ketones were investigated. Oxazaborolidine mediated reduction led to corresponding chiral alcohols generally in good yields and enantioselectivities up to 97% ee. Ruthenium-catalyzed transfer hydrogenation was rather unsuccessful in reducing cyclic ferrocene ketones. Proline-derived activator together with trichlorosilane also proved to be an effective method for some substrates (up to 99% ee). Pronounced tendency of α-ferrocenyl ketones toward reductive deoxygenation was studied by DFT computational methods.
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