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The Ru(II) complexes of SDP and DPEN combined with t-BuOK in 2-propanol formed a very effective catalyst for the hydrogenation of simple aromatic ketones with high activity and enantioselectivity. The racemic alpha-arylcycloalkanones can also be hydrogenated by this system, providing alpha-arylcycloalkanols in excellent cis/trans stereoselectivity (>99:1) and enantioselectivity (up to 99.9%) for the cis isomer. In the study of the effect of the alkali metal cation in the hydrogenation of acetophenone using RuCl(2)(Tol-SDP)(DPEN) and RuCl(2)(Xyl-SDP)(DPEN) catalysts, we found that t-BuONa provided a faster reaction than t-BuOK, which indicated that the sterically hindered diphosphine ligands preferred the base with the smaller metal cation.
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Xie et al. (2005) studied this question.
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