Synthesis of 2‐Azanorbornanes via Strain‐Release Formal Cycloadditions Initiated by Energy Transfer
Yu‐Che Chang, Christophe Salomé, Thomas C. Fessard, M. Kevin Brown
Abstract
Rigid bicycles are becoming more popular in the pharmaceutical industry because they allow for expansion to new and unique chemical spaces. This work describes a new strategy to construct 2-azanorbornanes, which can act as rigid piperidine/pyrrolidine scaffolds with well-defined exit vectors. To achieve the synthesis of 2-azanorbornanes, new strain-release reagent, azahousane, is introduced along with its photosensitized strain-release formal cycloaddition with alkenes. Furthermore, new reactivity between a housane and an imine is disclosed. Both strategies lead to various substituted 2-azanorbornanes with good selectivities.
Topics & Concepts
Strain (injury)Formal synthesisEnergy transferTransfer (computing)ChemistryComputer scienceStereochemistryBiologyChemical physicsParallel computingAnatomyRadical Photochemical ReactionsFluorine in Organic ChemistrySynthesis and Catalytic Reactions