Heteroatom Chirality

Whilst chirality is well-explored at carbon atoms, many chemists overlook heteroatom chirality, not least because the synthesis of conformationally stable compounds is challenging. Here, we highlight recent syntheses of molecules which are chiral at nitrogen and oxygen. Armodafinil and Esomeprazole are anomalies in drug discovery because their chirality is not due to an sp3-hybridised carbon. Instead, Esomeprazole has an (S)-configured sulfoxide as a result of two different organic substituents, the oxygen and the lone pair of the sulfur atom. This isomer is the more active enantiomer, the eutomer.Today, pharmaceutical companies have to produ...