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Imidazolinium and amidinium salts as Lewis acid organocatalysts

DOI: 10.3762/bjoc.8.205

Keywords: Diels–Alder , ionic liquids , organocatalysis , soft Lewis acids , thiiranes , thioesters

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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.

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