Stereoselective synthesis of diamines

Also involved: Dr. A. Gualandi, L. Cerisoli

Bis-homoallylic-1,2-diamines can be transformed in different bicyclic compounds exploiting the activation of the alkene double bond(s) by suitable electrofiles. For example, the iodine-mediated cyclization of differently substituted, optically pure 4,5-diamino-1,7-octadienes leads to substituted 2,5-diaza[2.2.1]diazabicyclooctanes. Electrophile-mediated cyclizations of optically pure 1,2-diaminocyclohex-4-ene are currently being investigated as a route to 2-amino-7-azabicyclo[2.2.1]heptane with potential pharmacological activity.

References

• G. Alvaro, R. Di Fabio, A. Gualandi, C. Fiorelli, M. Monari, D. Savoia, L. Zoli: “Stereoselective synthesis of substituted 2,5-diazabicyclo[2.2.1]heptanes by iodine-mediated cyclization of optically pure compounds containing the 4,5-diamino-1,7-octadiene and 1,2-diamino-4-alkene moieties”, Tetrahedron 2007, 63, 12446-12453.
• S. Grilli, G. Martelli, D. Savoia, C. Zazzetta: “Progress towards the stereoselective synthesis of 3,6-disubstituted 1,2-diamino-4-cyclohexenes by ring closing metathesis reaction”; Adv. Synth. Catal. 2002, 344, 1068.
• C. Boga, C. Fiorelli, D. Savoia: “Stereoselective synthesis of 3,6-disubstituted-1,2-diaminocyclohexanes through ring closing metathesis of 4,5-diamino-1,7-octadienes derivatives”, Synthesis 2006, 285-292.