Materials that respond to an electric or magnetic signal are crucial to many modern technologies, including data storage, ultrasound sensors and low temperature cooling. They also exhibit fascinating fundamental phenomena as seen by the awarding of the 2016 Nobel Prize for theoretical understanding of topological phases. Recently new classes of materials that contain both inorganic and organic building blocks have attracted attention for their ability to exhibit such magnetic and electronic functionalities.

Phase transfer reactions using chiral cations and inorganic basic salts such as hydroxides and carbonates are but a sub-set of a larger group of reactions known as chiral cation ion-pairing catalysis. Herein, we report three reactions using chiral dicationic bisguanidinium ion pairs as catalysis; they are are each paired with three different organometallic anions – permanganate, tungstate and molybdate. The ion pairs-catalyzed asymmetric oxidation of alkenes and sulfoxidation respectively.