Enantio- and Diastereoselective Assembly of Multi-layer Folding Chiral Targets via Asymmetric Catalytic Single C-C Formation

This work presents the first enantio- and diastereoselective assembly of multi-layer folding targets through asymmetric catalytic C-C bond formation. Pd[(S)-BINAP]Cl2 was found to be an efficient catalyst for Suzuki-Miyaura coupling between phosphinyl bromides and benzo thiadiazole boronic esters for this asymmetric assembly. The resulting chiral multi-layer folding framework was unambiguously determined by X-ray structural analysis showing a nearly parallel pattern of three layers and quasi-syn and -anti configurations. Good to excellent diastereo- and enantioselectivities (up to > 20:1 dr and > 99:1 er) have been achieved.