Stereospecific Photoredox-Catalyzed Vinylations to Functionalized Alkenes and C-Glycosides** |
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| Authors: | Dr Kumar Bhaskar Pal Dr Ester Maria Di Tommaso Dr A Ken Inge Prof Berit Olofsson |
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| Institution: | 1. Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, 10691 Stockholm, Sweden;2. Department of Materials and Environmental Chemistry, Stockholm University, 10691 Stockholm, Sweden |
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| Abstract: | We report an efficient radical-mediated C?C coupling through photoredox-catalyzed reactions of 4-alkyl-dihydropyridines (DHPs) and vinylbenziodoxol(on)es (VBX, VBO). This transition-metal-free and mild photocatalytic method has excellent functional group tolerance and affords vinylated products in good yields, with complete retention of the alkene configuration. The utility of the methodology is demonstrated by the diastereoselective synthesis of C-vinyl glycosides. Preliminary mechanistic studies suggest that the C?C bond formation is stereospecific and proceeds through a concerted radical coupling transition state. |
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| Keywords: | Alkenes Glycosides Hypervalent Iodine Compounds Photoredox Catalysis Vinylbenziodoxolones |
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