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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

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

Frings Marcus M   Thomé Isabelle I   Bolm Carsten C  

Beilstein journal of organic chemistry 20120903


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 ster  ...[more]

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