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.
Highlights
IntroductionBeing monoaza analogs of sulfones, sulfoximines have fascinated researchers from both academia and industry
Since their discovery in the middle of the last century, sulfoximines 1 (Figure 1) represent an important compound class among the comprehensive group of organosulfur reagents [1,2,3,4].Being monoaza analogs of sulfones, sulfoximines have fascinated researchers from both academia and industry
Scheme 1: Synthesis of compound (S)-3. This kind of addition was first described by Wehr in 1965 who allowed a number of isothiocyanates to react with dimethylsulfoximine [50]
Summary
Being monoaza analogs of sulfones, sulfoximines have fascinated researchers from both academia and industry. Because of their interesting chemical properties and the biological activities found for several derivatives, the use of sulfoximines has been explored in numerous applications. In agricultural chemistry it was discovered that sulfoximines can improve plant growth or act as insecticides in crop protection [5,6,7,8,9]. Further exemplary contributions come from medicinal chemistry where sulfoximines show potential as enzyme inhibitors [10,11,12,13,14], and from materials science where they were evaluated as functional building blocks [15]. Sulfoximines are most present in synthetic organic chemistry for Beilstein J.
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