Use of hypervalent ionide compounds and MBH carbonates in organocatalysis

Abstract

Beside transition-metal and enzymatic catalysis plays organocatalysis an important role in asymmetric organic sythesis. In the field of organocatalysis are amines group of compounds commonly used as organocatalysts. This thesis deals with the use of hypervalent iodine compounds in combination with amine catalysis and also with the use of Morita-Baylis-Hillman carbonates in organocatalytic allylic substitution reactions. In the first part an organocatalytic enantioselective α-selenylation reaction of saturated aldehydes using diphenyldiselenide and iodobenzene diacetate is described. Reaction is catalysed by commercially available first generation MacMillan catalyst. The products of the reaction were obtained in yields of 51-70 % and enantiomeric excess 95-99 %. Designed methodology was extended on the derivatives of β-ketoesters by catalysis of tertiary amines and quaternary ammonium salts. Apart from selenylation reactions we have also dealt with the possibility of formation C-C bond using hypervalent iodine compouds. Particularly, we focused on electrophillic alkynylation reactions of appropriate nucleophiles using acetylene-bearing hypervalent iodine compounds. Fluorinated sulfone derivatives and enolizable heterocycles such as pyrazolone derivatives, rhodanines, oxindoles and azlactones were..

    Similar works