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

Publication Type Scientific article indexed in SCOPUS or WOS database
Funding for basic activity Unknown
Defending: ,
Publication language English (en)
Title in original language Novel 3-C-Aminomethyl-Hexofuranose-Derived Thioureas and Their Testing in Asymmetric Catalysis
Field of research 1. Natural sciences
Sub-field of research 1.4 Chemical sciences
Authors Māris Turks
Evija Rolava
Dmitrijs Stepanovs
Anatolijs Mišņovs
Dean Markovic
Keywords carbohydrate, asymmetric Michael addition, nitrostyrene, glucose
Abstract 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.
DOI: 10.1016/j.tetasy.2015.07.003
Hyperlink: http://www.sciencedirect.com/science/article/pii/S0957416615002347 
Reference 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, pp.952-960. ISSN 0957-4166. Available from: doi:10.1016/j.tetasy.2015.07.003
Additional information Citation count:
ID 20586