PhD ceremony: Mr. J.F. Teichert, 16.15 uur, Academiegebouw, Broerstraat 5, Groningen
Title: Catalytic asymmetric synthesis of heterocycles
Promotor(s): prof. B.L. Feringa
Faculty: Mathematics and Natural Sciences
The research carried out in this thesis was directed towards the development of new, catalytic asymmetric transformations for the efficient and selective synthesis of heterocyclic compounds. These molecules are important synthetic intermediates for the preparation of biologically active compounds, such as in pharmaceuticals.
The methodologies used in this work comprise asymmetric copper-catalyzed allylic substitution, copper-catalyzed conjugate addition and iridium-catalyzed allylic substitutions.
Through copper-catalyzed allylic substitution reactions chiral nitrogen-containing heterocycles are available in combination with ring-closing metathesis. One important feature of these reactions is that it opens up a variable entry to a number of different ring sizes.
Employing copper-catalyzed conjugate addition reactions of Grignard reagents on coumarin derivatives, the corresponding conjugate addition products are available in high yields and enantioselectivities. It was found that the addition products serve as versatile synthetic intermediates, as they could be converted in situ into previously unavailable chiral phenolic esters and amides.
One of the highlights of this work is represented by the development of the first intramolecular asymmetric iridium-catalyzed allylic amidation. This new transformation opens up a synthetic pathway towards chiral tetrahydroisoquinolines and chiral saturated nitrogen heterocycles. Chiral tetrahydroisoquinolines are key structural features of a vast number of biologically active products.
Previously, very few synthetic entries towards these products existed.
Three researchers of the Faculty of Science and Engineering have been awarded an ENW-XS grant by the Dutch Research Council (Nederlandse Organisatie voor Wetenschappelijke Onderzoek, NWO): Prof. A.I. Guskov the Groningen Biomolecular Sciences and...
Bayu Jayawardhana has been appointed scientific director of DISC, the interuniversity research institute and graduate school that unites all university groups in the Netherlands that are active in systems and control theory and engineering. The...
Researchers Clemens Mayer and Danny Incarnato of the University of Groningen have been awarded an ERC Consolidator Grant.
The UG website uses functional and anonymous analytics cookies. Please answer the question of whether you want to accept
or reject other cookies (such as tracking cookies).
If no choice is made, only basic cookies will be stored. More information