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Novel 3-C-aminomethyl-hexofuranose-derived thioureas and their testing in asymmetric catalysis

Both 1, 2:5, 6-di-O-isopropylidene- and 1, 2:5, 6-di-O-cyclohexylidene-α-d-glucofuranose-derived ketones provided the corresponding branched 3-C-nitromethyl-congeners in the Henry reaction with nitromethane anion. Reduction of the nitro moiety followed by derivatization with iso(thio)cyanates gave 3-C-aminomethyl-hexofuranose-derived (thio)ureas. The relative configuration of the products in each series was unambiguously established by X-ray analysis. The title products were shown to act as organocatalysts in Friedel–Crafts alkylations of indoles with β-nitrostyrenes and in Michael additions of nitromethane to trans-chalcones.

3-C-aminomethyl-hexofuranose-derived thioureas; asymmetric catalysis

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