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Construction of All-Carbon Quaternary Stereocenters by Scandium-Catalyzed Intramolecular C-H Alkylation of Imidazoles with 1,1-Disubstituted Alkenes.

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The exo-selective C-H cycloaddition of imidazoles to 1,1-disubstituted alkenes has been achieved for the first time by using half-sandwich scandium catalysts. A wide range of imidazole compounds bearing various 1,1-disubstituted… Click to show full abstract

The exo-selective C-H cycloaddition of imidazoles to 1,1-disubstituted alkenes has been achieved for the first time by using half-sandwich scandium catalysts. A wide range of imidazole compounds bearing various 1,1-disubstituted aliphatic alkenes, styrenes, dienes and enynes have been selectively converted in high yields to the corresponding bicyclic imidazole derivatives bearing -all-carbon-substituted quaternary stereocenters. By using a chiral half-sandwich scandium catalyst, the asymmetric exo-selective cyclization has also been achieved with a high level of enantioselectivity.

Keywords: construction carbon; carbon quaternary; quaternary stereocenters; imidazoles disubstituted; disubstituted alkenes

Journal Title: Journal of the American Chemical Society
Year Published: 2020

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