PhD ceremony Ms. M. Hanstein: Asymmetric catalysis in the synthesis of cis-cyclopropyl containing fatty acids and the addition of Grignard reagents to carbonyl compounds

PhD ceremony: Ms. M. Hanstein

Dissertation: Asymmetric catalysis in the synthesis of cis-cyclopropyl containing fatty acids and the addition of Grignard reagents to carbonyl compounds

Promotor(s): prof. A.J. Minnaard

Faculty: Mathematics and Natural Sciences

The work described in the first part of this thesis is about the synthesis of compounds, e.g. lipids and fatty acids, isolated from the cell wall of bacteria. The cell wall defines the inside of the cell from its surrounding, and functions as a protective barrier. A distinct example of a cell wall, with a low permeability, is the cell wall of Mycobacterium tuberculosis. Due to this characteristic of the cell wall, treatment with therapeutics is difficult. For a better insight into this problem, biochemists need isolated cell wall components to investigate this phenomenon. Since Mycobacterium tuberculosis is a slow growing bacterium and requires specific research facilities, the synthesis of those compounds by chemist provides an alternative.

The second part of this thesis is about a new methodology, lately developed in our institute. With this methodology chiral secondary and in particular tertiary alcohols can be synthesized in a single step by the copper(I)-catalyzed addition of Grignard reagents to either aldehydes or ketones. The development of new methodologies is essential in the field of chemistry in order to improve existing procedures as well as to develop novel routes for the synthesis of natural products. Nowadays the development of such a methodology requires not only regio- and stereospecificity, but also atom economy gets important to make chemical processes more sustainable.