Development of enantioselective carbon-carbon and carbon-heteroatom bond-forming reactions using Brønsted acids.
Contact person and project supervisor: Assoc. Prof. Jan Veselý, jan.vesely@natur.cuni.cz
WWW: http://orgchem.cz/vesely/
Research group: Group of Asymmetric Synthesis (GAS)
Leader of the research group: Assoc. Prof. Jan Veselý, Ph.D.
Department: Department of Organic Chemistry
Project summary:
The power of Brønsted acids (BAs) in catalysis is recognized since the beginning of organic synthesis. Nevertheless, their use as catalysts in asymmetric approaches was underestimated until the end of 20th century. Nowadays, chiral BAs are used for a range of carbon-carbon bond-forming reactions, where BAs are responsible for activation of carbonyl, imine, alkene, alkyne and hydroxy groups. Recently, Lambert and coworkers introduced a novel carbon acid platform that could be used for enantioselective BA catalysis, chiral pentacarboxycyclopentadienes (PCCPs, Figure 2). The acidity of PCCP is sufficiently high due to aromatic character of the PCCP platform together with inductive effect of electronegative groups present. To date, the efficiency of PCCP catalysts was demonstrated in only a few types of C-C and C-S forming reactions. Considering the above and our interest in enantioselective preparation of (hetero)cycles, this PhD project will focus on development of new bifunctional catalyst containing PCCP platform and their application to enantioselective synthesis and functionalization of (hetero)cyclic compounds. Additionally, processes including multifunctional catalysis and co-operative catalysis will be also studied.
Profile of an ideal candidate: MSc. or equivalent in Chemistry (required), good knowledge of English and Organic Synthesis is an advantage.
