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A variety of highly functionalized 2\u2010amino\u20105\u2010hydroxyvaleric acid esters or peptides bearing 1,4\u2010non\u2010adjacent stereogenic centers have been prepared in high yields with excellent enantio\u2010 and diastereoselectivity. Judicious selection and rational modification of the Ru catalysts with careful tuning of the reaction conditions played a pivotal role in stereoselectivity control as well as attenuating undesired \u03b1\u2010epimerization, thus enabling a full complement of all four stereoisomers that were otherwise inaccessible in previous work. 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