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

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.

SUBMITTER: Frings M 

PROVIDER: S-EPMC3458769 | biostudies-literature | 2012

REPOSITORIES: biostudies-literature