In Nov. 2019, the manuscript titled “Bidirectional enantioselective synthesis of bisbenzofuran atropisomeric oligoarenes featuring two distal C–C stereogenic axes” was accepted by Chemical Science. This work was contributed by Dr. Bao Xiaoze from the group of Marine Drugs in the College of Pharmaceutical Science, Zhejiang University of Technology.

    In recent years, molecules featuring chiral axis were widely found in natural products, drugs, asymmetric catalysis, and functional materials. The importance of axial chirality was well-realized by scientist. However, the enantioselective construction of chiral axis tethered to a five membered aromatic heterocycle was difficult because of the low rotation barrier. On the other hand, oligoarenes are long pi-conjugated systems commonly used in functional materials and asymmetric catalysis. The oligoarenes bearing multiple stereogenic axes are particularly attractive with their unique topologies, but their efficient enantioselective synthetic access remains a challenging task.

    In this context, during his further study in France, Doc. Bao Xiaoze accomplished the enantioselctive synthesis of oligoarenes featuring two furan atropisomers with the collaboration with Prof. Jean Rodriguez and Associated Professor Damien Bonne in iSm2. The construction of this unique oligoarenes was highly facilitated by the efficient double central-to-axial chirality conversion. In addition, the stereodivergent synthesis of this atropisomers was conducted, which was significant for the investigation of their properties. The high efficiency and easy operation of this central-to-axial chirality conversion strategy may have potential application in natural product and drug synthesis.

Link to the paper:

https://pubs.rsc.org/en/content/articlelanding/2020/sc/c9sc04378k#!divAbstract