Zhyhadlo Y. Synthesis of di- and polysubstituted cage hydrocarbons

The dissertation is devoted to the development of methods for the synthesis of di- and polysubstituted cage compounds (adamantane, diamantane, C2 bishomocubane, Cs- and D3-trishomocubanes).It was found that Rh2(OAc)4 is an efficient catalyst for intramolecular C-H amination of cage sulfamates. This enabled development of method for the synthesis of a number of cyclic sulfamidates that contain adamantane, diamantane, or noradamantane cages. It was discovered that the cage sulfamidates are convenient synthons for the synthesis of wide variety of 1,2-disubstituted adamantane and diamantane amines. Feasibility of the conversion of sulfamidate group into sulfonimide, keto alcohol, and amino alcohol was tested on adamantane-based sulfamidate. The cage’s aminoalcohol was used for the synthesis of Vildagliptine bioisosters.