Enantio- and Diastereoselective Assembly of Multi-Layer Folding Chiral Targets via Asymmetric Catalytic Single C-C Bond 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]Cl-2 is found to be an efficient catalyst for the Suzuki-Miyaura coupling between phosphinyl bromides and benzothiadiazole boronic esters for this asymmetric assembly. The structure of the resulting chiral multi-layer folding framework is unambiguously determined by X-ray analysis and shows 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) are achieved.