Beilstein Journal of Organic Chemistry 2012-01-01

Synthesis of chiral sulfoximine-based thioureas and their application in asymmetric organocatalysis.

Marcus Frings, Isabelle Thomé, Carsten Bolm

Index: Beilstein J. Org. Chem. 8 , 1443-51, (2012)

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Abstract

For the first time, chiral sulfoximine derivatives have been applied as asymmetric organocatalysts. In combination with a thiourea-type backbone the sulfonimidoyl moiety leads to organocatalysts showing good reactivity in the catalytic desymmetrization of a cyclic meso-anhydride and moderate enantioselectivity in the catalytic asymmetric Biginelli reaction. Straightforward synthetic routes provide the newly designed thiourea-sulfoximine catalysts in high overall yields without affecting the stereohomogeneity of the sulfur-containing core fragment.