Enantiopure sulfoxides and quinones: from the synthesis of natural products to molecular switches

Abstract

Sulfoxides are widely used in asymmetric synthesis due to their high efficiency as chiral inducers in numerous transformations. This article highlights the most significant contributions to the field of asymmetric synthesis with sulfoxides developed in the research group at the UAM. Total synthesis of natural products using diastereoselective reductions of β-ketosulfoxides, Diels-Alder reactions with 2-p-tolylsulfinylquinones or conjugate additions as key steps, are included. The reported synthetic approach to enantiopure helicenequinones is also revised. New uses of sulfoxides in the design of enantiopure molecular switches, are also shown.