Novel 3-C-Aminomethyl-Hexofuranose-Derived Thioureas and Their Testing in Asymmetric Catalysis

Tetrahedron: Asymmetry 2015
Māris Turks, Evija Rolava, Dmitrijs Stepanovs, Anatolijs Mišņovs, Dean Markovic

Both 1,2:5,6-di-O-isopropylidene- and 1,2:5,6-di-O-cyclohexylidene-a-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 b-nitrostyrenes and in Michael additions of nitromethane to trans-chalcones.

Atslēgas vārdi
carbohydrate, asymmetric Michael addition, nitrostyrene, glucose
DOI
10.1016/j.tetasy.2015.07.003
Hipersaite
http://www.sciencedirect.com/science/article/pii/S0957416615002347

Turks, M., Rolava, E., Stepanovs, D., Mišņovs, A., Markovic, D. Novel 3-C-Aminomethyl-Hexofuranose-Derived Thioureas and Their Testing in Asymmetric Catalysis. Tetrahedron: Asymmetry, 2015, Vol.26, Iss.17, 952.-960.lpp. ISSN 0957-4166. Pieejams: doi:10.1016/j.tetasy.2015.07.003

Publikācijas valoda
English (en)