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

Date

2003-05-02

Author

Tanyeli, Cihangir
Özçubukçu, Salih

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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%.

Subject Keywords

Physical and Theoretical Chemistry, Inorganic Chemistry, Organic Chemistry, Catalysis

URI

https://hdl.handle.net/11511/34868

Journal

Tetrahedron Asymmetry

DOI

https://doi.org/10.1016/s0957-4166(03)00161-7

Collections

Department of Chemistry, Article

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Citation Formats

C. Tanyeli and S. Özçubukçu, “The first enantioselective synthesis of chiral norbornane-type 1,4-diamine ligand,” Tetrahedron Asymmetry, pp. 1167–1170, 2003, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/34868.