Enantioselective hydride abstraction in organic substrates: future applications for chiral carbenium ions

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]