TY - JOUR A1 - Frings, Marcus A1 - Thomé, Isabelle A1 - Bolm, Carsten T1 - Synthesis of chiral sulfoximine-based thioureas and their application in asymmetric organocatalysis JF - Beilstein Journal of Organic Chemistry PY - 2012/// VL - 8 SP - 1443 EP - 1451 SN - 1860-5397 DO - 10.3762/bjoc.8.164 PB - Beilstein-Institut JA - Beilstein J. Org. Chem. UR - https://doi.org/10.3762/bjoc.8.164 KW - anhydride opening KW - catalytic asymmetric Biginelli reaction KW - organocatalysis KW - sulfoximines KW - thioureas N2 - 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. ER -