Tunable [3+2] and [4+2] annulations for pyrrolidine and piperidine synthesis

N-heterocycles are privileged pharmaceutical scaffolds in drug discovery and development. We disclose here divergent intermolecular coupling strategies that can access diverse N-heterocycles directly from olefins. The radical-to-polar mechanistic switching is key for the divergent cyclization processes. These distinctive annulations result in the coupling of alkenes with simple bifunctional reagents for divergent N-heterocycle syntheses.

Automated summary

We describe a diversified intermolecular coupling strategy that enables the direct synthesis of diverse N-heterocycles from olefins. The switching between radical and polar mechanisms is crucial for the divergent cyclization processes. These unique annulations involve the coupling of alkenes with simple bifunctional reagents for the synthesis of diverse N-heterocycles.