DNA-based asymmetric catalysis as a synthetic tool

PhD ceremony: Mr. R.P. Megens, 16.15 uur, Academiegebouw, Broerstraat 5, Groningen

Dissertation: DNA-based asymmetric catalysis as a synthetic tool

Promotor(s): prof. J.G. Roelfes

Faculty: Mathematics and Natural Sciences

The helical structure of DNA has always attracted special attention from chemist. In our group a concept was developed in which DNA is used in order to obtain enantioselective catalysis. This concept is based on an achiral metal complex which can bind non-covalently to the DNA. The helicity of the DNA is hereby transferred to the metal complex, which can be subsequently transferred onto a variety of asymmetrically catalyzed reactions, like the Diels-Alder reaction, the Michael addition, the Friedel-Crafts alkylation and more recently the syn-hydration reaction.

In this thesis an investigation on the use of this concept in synthetically interesting reactions is discussed. The research was focused in two directions. First the optimization of the reaction conditions in order to improve the scale of the reactions and the recycling of the catalyst after use. Secondly, the development of new reactions which were unknown or hard to perform, prior to this research.