Project description
Expanding tractable stereochemical space by stereoselective catalysis
Stereoisomers are molecular entities with identical atomic connections existing in separate forms due to the different arrangements of their atoms in space. Most stereogenic units encode two configurations, describing distinct three-dimensional molecular structures. These strongly impact molecular properties, which prompts preparative methods with control over configuration, ideally using catalysts that enable selective transformations. The catalysts differentiate competing reaction pathways towards the desired stereoisomer and remain intact throughout the process. The aim of the EU-funded X-Fold StereoGen project is now to catalytically control stereogenic units that encode more than two configurations. Besides the larger stereochemical space addressable by stereoselective synthesis, the conceptual interconnection between higher-order stereogenicity and conformational space is endeavored.
Objective
Catalytic, stereoselective methodologies to study the control over the configuration of stereogenic elements with three- four-, five- and six-fold stereoisomerism are proposed. Previous catalyst-stereocontrolled methods allowed the differentiation of a twofold number of stereoisomers for any given stereogenic element. It is thus anticipated that expanding the stereogenicity in stereoselective catalysis represents a significant advance for the field. The reunification of conformational analysis and stereoisomerism in organic synthesis is expected to provide an improved conceptual framework. Traditionally, stereogenic elements are considered to generate a doubled number of possible stereoisomers, which are assigned with standard stereochemical descriptors such as R and S. The overall number of possible stereoisomers in a molecule with a set of stereogenic elements (n) is thus commonly predicted as 2^n. This binary stereochemical understanding of stereoisomerism represents a current basis for organic synthesis and a wide range of bioactive compounds critical for our health care are skillfully prepared by controlling the configuration of desired stereoisomers. Control over stereogenic elements that generate more than a twofold number of possible stereoisomers thus dramatically extents the scope of current stereoselective catalysis and organic synthesis. 1: The underpinnings of conformational analysis and the catalyst-stereocontrolled synthesis will be conceptually unequivocally reunited. 2: The uncharted setting of catalyst control over three-, four-, five- and six-fold stereogenicity will be established by the development of versatile synthetic methodologies. 3: Novel molecular architectures featuring unique chemical topologies will be assessible, representing unexplored chemical designs for a broad range of applications. 4: A divergent catalysis approach will be explored, utilizing common substrates for several stereoisomeric products with extended stereogenicity.
Fields of science (EuroSciVoc)
CORDIS classifies projects with EuroSciVoc, a multilingual taxonomy of fields of science, through a semi-automatic process based on NLP techniques. This project's classification has been validated by the project's team.
CORDIS classifies projects with EuroSciVoc, a multilingual taxonomy of fields of science, through a semi-automatic process based on NLP techniques. This project's classification has been validated by the project's team.
Programme(s)
Funding Scheme
ERC-COG - Consolidator GrantHost institution
4051 Basel
Switzerland