To explore and optimize the asymmetric synthesis of S-trifluoromethyl sulfoxide and sulfoximine pharmacophores.
Cleavage of acyl group to form free-NH sulfilimine
Hydrolysis via backside displacement of amine resulting in sulfoxide formation
Inversion of stereochemistry observed during the synthesis.
Successful synthesis of S-trifluoromethyl sulfoxide with clear stereochemical inversion.
Formation of sulfoximine linked to hydrolysis of sulfilimine.
Novel pathways identified for potential drug development.
Abstract
-acyl group is first cleaved to give the free-NH sulfilimine that then undergoes hydrolysis by backside displacement of the amine to give the sulfoxide with inversion of stereochemistry.