Synthesis of various camphor-based chiral pyridine derivatives

Thesis Type: Postgraduate

Institution Of The Thesis: Middle East Technical University, Faculty of Arts and Sciences, Department of Chemistry, Turkey

Approval Date: 2005

Thesis Language: English

Student: Murat Işık



Chiral aromatic nitrogen heterocycles are finding many applications in asymmetric organic synthesis, particularly as ligands in the preparation of chiral metal complexes. Since camphor-based chiral auxiliaries are known to be especially effective, a number of pyridines fused to the camphor skeleton have been reported. It is well known that nicotinic acid and its derivatives exhibiting qualitatively the biological activity of nicotinamide, which acts as an electron acceptor in many biological redox reactions. In connection to our works, we attempted to develop short and convenient way to prepare various camphorderived chiral pyridine or nicotinic acid derivatives. Here we report our results obtained from the annulation of (+)- b- hydroxymethylenecamphor as the feasible chiral pool with various enamines derived from active methylene compounds. (+)- b- Hydroxymethylenecamphor prepared from cheap and easily available natural (+)-camphor and enamines were transformed into chiral camphor-based pyridine derivatives via tandem condensation reaction in good yields.