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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]

PMID: 23019479

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