MultiChiral

The goal of the MultiChiral project is the design of a unified enantioselective strategy combining organocatalysis with conversion of chirality for accessing original molecules featuring multiple stereogenic elements, with a special focus to the challenging control of axial and helical chiralities. The general pathway involves the organocatalytic enantioselective cyclization of simple well-designed achiral precursors into partially saturated cyclic intermediates bearing either central/helical or central/axial chiralities. They will be transformed during an aromatization step that converts the central chirality into the axial chirality, generating molecules with either axial/helical, di-axial, tri-axial or di-axial/helical chirality. The absolute configuration of final products will be characterized using chiroptical spectroscopies and single crystal X-ray diffraction (SCXRD). The second axis of the project will focus on the crystalline state of the heterohelicenes and more specifically on obtaining chiral supramolecular organizations by screening the crystallization conditions. The chiral properties of these materials will be studied in detail using the complementarity of SCXRD, chiroptical spectroscopies and DFT calculations. A very close collaboration between synthetic organic chemists, theoretical chemists, and physical chemists will be required for the success of this project.