The next CMC seminar will be held on September 17th (10.30 am) in room Génome with a presentation from Erica Benedetti (Université de Paris). The title and abstract can be found below.Presentation title: Synthesis and applications of planar chiral [2.2]paracyclophanesAbstract: Originally discovered in a serendipitous fashion by vapour phase pyrolysis of p-xylene, [2.2]paracyclophane (pCp) and its derivatives have rapidly gained popularity amongst chemists due to their unique three-dimensional architecture that can give rise to planar chirality. Despite their broad range of applications, optically active paracyclophanes are currently still mainly obtained through enantiomers separation by chromatography on chiral stationary phases. The optimization of new asymmetric processes providing a practical access to chiral pCps can therefore be considered as a priority in modern cyclophane chemistry.
We have developed a general approach based on asymmetric transfer hydrogenations (ATH) for controlling the planar chirality of a range of substituted [2.2]paracyclophanes. Our strategy enables us to perform both the kinetic resolution of racemic compounds and the desymmetrization of centrosymmetric meso derivatives on synthetically useful scales. The obtained enantioenriched derivatives, which incorporate different reactive groups on each ring of the pCp core, can be used as key intermediates for the preparation of new circularly polarized light emitting dyes (CPL). Based on its broad applicability, we are convinced our method will reveal to be an extremely useful tool to rapidly access complex planar chiral [2.2]paracyclophanes in their enantiopure form.
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