The first enantioselective synthesis of chiral norbornane-type 1,4-diamine ligand

2003-05-02
The asymmetric synthesis of trans-2,3-bis(aminomethyl)norbornane was performed starting with endo-2,3-norbornene dicarboxylate anhydride. Desymmetrization of meso-anhydride 1 and following selective epimerization gave the trans-monoester (+)-3 with a high enantiomeric excess (98% e.e.). LiAlH4 reduction of the trans-monoester to the 1,4-diol, which was then treated with phthalimide under Mitsunobu conditions and, following a Gabriel type amine synthesis with hydrazine hydrate, yielded a saturated and unsaturated diamine mixture. Hydrogenation of mixture finally afforded saturated diamine (+)-8 with a yield of 37%.

Citation Formats
C. Tanyeli and S. Özçubukçu, “The first enantioselective synthesis of chiral norbornane-type 1,4-diamine ligand,” Tetrahedron Asymmetry, vol. 14, no. 9, pp. 1167–1170, 2003, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/34868.