Asymmetric Ring Opening of Epoxides and Aziridines with Carbon Nucleophiles

Three-membered heterocyclic rings offer a powerful combination of reactivity, stability, availability, and atom economy. While the use of heteroatom-based nucleophiles has been successfully employed, the use of carbon-centered nucleophiles has been less developed yet represents a significant advance since it build the basic carbon framework. In fact, the asymmetric ring opening of epoxides and aziridines with carbon-based nucleophiles, as will be discussed in this microreview, offers the possibility of generating valuable chiral non-racemic building blocks in a very simple manner and in a stereodefined fashion.