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

• Main Authors: Marcus Frings, Isabelle Thomé, Carsten Bolm
• Format: Article
• Language: English
• Published: Beilstein-Institut 2012-09-01
• Series: Beilstein Journal of Organic Chemistry
• Subjects: anhydride opening; catalytic asymmetric Biginelli reaction; organocatalysis; sulfoximines; thioureas
• Online Access: https://doi.org/10.3762/bjoc.8.164

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.