Enantioselective formal synthesis of pregabalin with bifunctional acid/base organocatalysts

Kapucu, Merve
Pregabalin, which is marketed under the brand name of Lyrica by Pfizer, is an important chiral drug in the treatment of epilepsy and neuropathic pain. Since only S-Pregabalin is active for the treatment, asymmetric synthesis was accomplished in 6 steps and the chiral induction was done by transition metal catalysis in industrial production. In this thesis, we applied an alternative synthetic route taken place in 3 steps. The key step comprised the chiral induction done by organocatalysis and the formal asymmetric synthesis of Pregabalin has been performed by Michael type addition of diethyl malonate to (E)-4-Methyl-1-nitro-1-pentene in 81% ee. Parallel to this work, different Michael acceptors and donors were used to test our catalyts’ activities.


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Citation Formats
M. Kapucu, “Enantioselective formal synthesis of pregabalin with bifunctional acid/base organocatalysts,” M.S. - Master of Science, Middle East Technical University, 2013.