A Hong Kong University of Science and Technology (HKUST) research team has developed a new method to address the challenges of synthesizing chiral bridged polycyclic structures, particularly those with a bridged seven-membered subunit.

This innovative approach utilizes 3-oxidopyrylium ylides to create the desired complex shapes, paving the way for more applications in the rapid synthesis and diversification of other valuable complex molecules, including important natural products and drug molecules.

Chiral bridged polycyclic structures, particularly those bearing a bridged seven-membered subunit, represent a complex and intriguing molecular architecture found in many natural and biologically significant compounds. However, synthesizing these structures has posed substantial challenges for chemists.

The research team successfully addressed the formidable challenge of preventing the formation of strained, anti-Bredt cycloadducts bearing bridge-head double bonds while exerting enantiocontrol. They achieved this through non-covalent activation by chiral acid catalysis, a novel approach compared to the traditional covalent activation methods.

Source: Phys.org

Image: Frontier molecular orbitals of (R)-1–3.