Imidazolinium and amidinium salts as Lewis acid organocatalysts

Abstract

The application of imidazolinium and amidinium salts as soft Lewis acid organocatalysts is described. These salts were suitable catalysts for the activation of unsaturated thioesters in a Diels–Alder reaction and in the ring opening of thiiranes and epoxides. The products were isolated in good yields. The mild catalysts did not cause desulfurization of the products containing a thiol or thiocarbonyl group.

Keywords

• Diels–Alder
• ionic liquids
• organocatalysis
• soft Lewis acids
• thiiranes
• thioesters