Abstract: Oxidation reactions are at the core of asymmetric chemistry. It is therefore surprising, in view of the potential applications, not to find any instances of the notion of using a "chiral cation" to distinguish between a pair of prochiral hydrides during hydride transfer [H-T]. To the best of our knowledge, there are none. Yet, the converse concept of using a "chiral anion" to distinguish between a pair of prochiral protons during a deprotonation has led to significant advancements in the field of asymmetric synthesis.[1] This letter describes the first example of an enantioselective [HT]