CuCAN · Asymmetric Copper Catalyzed Multicomponent Coupling

Asymmetric Copper Catalyzed Multicomponent Coupling

We have developed a copper-catalyzed approach to high value, functionalised nitrogen-containing molecular architectures by combining readily available feedstocks with high control of regiochemistry and absolute and relative stereochemistry. The enantioselective multicomponent coupling allows one-pot access to functionalised homoallylic amines (including those bearing quaternary stereocentres) that are privileged substructures in bioactive compounds and versatile precursors to other biologically-significant motifs. Our low-cost metal catalyzed enantioselective process also delivers N-heterocyclic building blocks whose value will be illustrated through efficient target syntheses of drugs, natural products and tools for biology. Our recent discovery of a copper-catalyzed borylative allylation of imines leaves us uniquely placed to meet this challenge. The development of operationally simple methods for the rapid and efficient, catalytic construction of high value products from simple starting materials is key to the future of synthetic science and thus society. Moreover, if high value chiral products can be assembled from several readily available achiral components in a one-pot process then diverse collections of important compounds can be quickly constructed by simple variation of the material inputs. Even more challenging, but attractive to the scientific community, would be a multicomponent process catalyzed by a low-cost metal using a commercially-available ligand to control the regiochemistry and relative and absolute stereochemistry of the cross-coupling process. In this project we have developed novel methodology for the construction of high value stereoselective amine compounds and applied it to the study of nitrogen based bioactive target synthesis. We have accomplished the project objectives by addressing three specific aims: AIM 1: Methodology development for enantioselective, multicomponent approach to high value amines AIM 2: Application of enantioselective method in bioactive target and library synthesis AIM 3: Methodology development for new multicomponent reaction

Data: CORDIS, © European Union