Chiral Cation Catalysis

Chiral cations have found useful applications as phase transfer catalyst i.e. in partnership with inorganic basic salts such as hydroxides and carbonates for basic reactions. We have over the past decade developed several chiral cation catalysts including pentanidium and bis-guanidinium. Herein, we report three topics related to these chiral cation catalysts. Firstly, we will discuss the role of these catalysts in ion pair catalysis. We will discuss reactions in which they are partnered with polyoxometalates such as tungstate and molybdate. We will also discuss reaction involving hypervalent silicate intermediates. In the second topic, we will discuss how we use these catalysts are used to investigate roles of halogen bonding in catalysis. Lastly, we will explain the desymmetrisation of sulfinate, which provide a route to a range of enantio-enriched sulfur stereogenic centers.