Asymmetrie hydrogenation of imines and enamines using phosphoramidite ligands
Promotie: mw. N. Mrŝić, 14.45 uur, Academiegebouw, Broerstraat 5, Groningen
Proefschrift: Asymmetrie hydrogenation of imines and enamines using phosphoramidite ligands
Promotor(s): prof.dr. J.G. de Vries, prof.dr. B.L. Feringa, prof.dr. A.J. Minnaard
Faculteit: Wiskunde en Natuurwetenschappen
Contact: Nataša Mršic, tel. 00 385 1372 2037, e-mail: n.mrsic@rug.nl
Asymmetrie hydrogenation of imines and enamines using phosphoramidite ligands
Asymmetric hydrogenation (AH) represents a versatile, clean and atom economic method for the preparation of enantiopure compounds. We were in particularly interested in the AH of heteroaromatic compounds such as quinolines, quinoxalines and indoles, due to the fact that chiral heterocyclic compounds are often found as part of the structures of pharmaceuticals and physiologically active compounds. In this thesis Nataša Mršic describes the AH of 2- and 2,6-substituted quinolines and quinoxalines catalyzed by iridium complexes of BINOL-derived phosphoramidites. Enantioselectivities of up to 89% and 96%, respectively, were obtained. Primary chiral amines were obtained via the asymmetric hydrogenation of N-aryl imines, followed by the subsequent deprotection of the secondary amines. Enantioselectivities up to >99% were obtained. We were also able to perform hydrogenation of indoles catalyzed by rhodium complexes with phosphoramidite ligands. Full conversions and enantioselectivities up to 74% were obtained in the hydrogenation of N-protected indoles. Finally, we developed a route to beta-amino acid derivatives via the AH of N-aryl beta-enamino acid esters. Full conversions and enantioselectivities of up to 70% were obtained using an Ir/phosphoramidite catalytic system. The products that are made by this technology are mostly used as building blocks for medicines and to a lesser extent also for agrochemicals and flavours and fragrances.
Last modified: | 13 March 2020 01.16 a.m. |
More news
-
16 April 2024
UG signs Barcelona Declaration on Open Research Information
In a significant stride toward advancing responsible research assessment and open science, the University of Groningen has officially signed the Barcelona Declaration on Open Research Information.
-
02 April 2024
Flying on wood dust
Every two weeks, UG Makers puts the spotlight on a researcher who has created something tangible, ranging from homemade measuring equipment for academic research to small or larger products that can change our daily lives. That is how UG...
-
18 March 2024
VentureLab North helps researchers to develop succesful startups
It has happened to many researchers. While working, you suddenly ask yourself: would this not be incredibly useful for people outside of my own research discipline? There are many ways to share the results of your research. For example, think of a...