Nitrogen-containing moieties are omnipresent in natural products, biologically active compounds and agricultural chemicals. In particular, the 8-azabicyclo[3.2.1]octane and 9-azabicyclo[3.3.1]nonane skeletons constitute the core of many natural tropane 1 and homotropane alkaloids, 2 respectively, and analogues presenting a wide range of biological activities. For instance, tropinone, cocaine and scopolamine (Figure ) are amongst the most popular representative examples of natural alkaloids presenting a 8-azabicyclo[3.2.1]octane (tropane) skeleton as their base structure. Unlike its natural enantiomer, unnatural (-)-ferruginine (Figure ), is a good agonist for nicotinic acetylcholine receptor (nAchR). The 9-azabicyclo [3.3.1]nonane (homotropane) skeleton can be found in the structure of (-)adaline, and (+)-euphococcinine (Figure ), two important defensive alkaloids from, respectively, the European ladybug Adalia bipunctata and the Australian ladybug Cryptolaemis montrouzieri. Mannich reaction, access to tropanes and related alkaloids has been the object of intense activity. Strategies based on ionic reactions, cycloadditions and transition metal mediated processes have been reported. Despite its attractiveness to build cycles, radical processes have only been scarcely used. The development of a general and flexible access to tropane related heterocycles using a mild radicalbased approach is expected to complement nicely the existing methods. To gain in efficiency, a cascade processes involving consecutive formation of C-C bonds is particularly sought. The biosynthesis of tropane alkaloids as well as Robinson biomimetic synthesis are both based on an ionic [3+3]annulation processes involving 1,3-bis-iminium ions and 1,3-bis-enolates synthons (Scheme 1, A).