A general route to mono- and disubstituted divinyl sulfones: acyclic michael acceptors for the synthesis of polyfunctionalized cyclic sulfones

Abstract

Nucleophilic C−S bond formation using easily available β-hydroxysulfonate derivatives allowed direct access to new mono- and disubstituted divinyl sulfones. Our strategy uses thioethanol (HSCH₂CH₂OH) and its analogues such as HSCH₂CH(Y)OH generated in situ. The strategy also allows the synthesis of modified divinyl sulfones attached to chiral appendages like carbohydrates. Bis-heteronucleophilic Michael addition reactions with 1 equiv of a primary amine afforded new generations of S,S-dioxothiomorpholine derivatives known for their therapeutic applications. Further synthetic manipulations of some of these cyclic compounds led to the synthesis of novel bicyclic derivatives.