Laboratory of Organic Chemistry

Specific synthetic studies

Design of biomimetic catalysts

Anssi Haikarainen, Jussi Sipilä

During recent years chiral salen-type transition metal complexes have emerged as highly efficient catalysts for various important reactions ranging from oxidations to carbon-carbon bond formations. These complexes with the general structure shown below [salen = N,N'- bis(salicylaldehydo)ethylenediamine] may also bear potentially stereogenic carbon centers in the vicinity of the metal binding site.

The main topics of this project are: 1 ) the syntheses of salen-type transition metal complexes that can be used as catalysts in biomimetic oxidations (oxidation of benzylic position in aromatic compounds, epoxidation of alkenes, oxidation of sulfides to sulphoxides), 2 ) the design of practical oxidation systems (oxidant, cocatalysts) for salen-catalyzed oxidation of lignocellulosic materials and epoxidation of alkenes and 3) asymmetric oxidation of alkenes and asymmetric oxidative coupling of cinnamyl alcohols.

The synthesis and structure determination (X-ray crystallography) of various type salen complexes have been performed in collaboration with the Laboratory of Inorganic Chemistry at UH. The project is also in collaboration with the University of Milan (Prof. M. Orlandi). (Haikarainen, Sipilä, P. Pietikäinen and G. Brunow)