Novel studies on the chemoenzymatic synthesis of polychlorinated bicyclic systems and the synthesis of C2 and C3 symmetric chiral ligands

Türkmen, Yunus Emre
Optically active polychlorinated bicyclic systems are important starting materials for the synthesis of complex target molecules. In the first part of the study, the syntheses of several racemic and meso hexachloronorbornene derivatives were executed successfully, starting from hexachlorocyclopentadiene. The enantio-enriched acetoxymethyl derivative (-)-2 and the hemiester (-)-6 were synthesized in high e.e. values by using several hydrolase type enzymes. The absolute configuration of (-)-2 was determined by transforming it to the corresponding norbornene derivative (-)-7 with known absolute configuration. In the second part of the study, C2 symmetric chiral ligand (-)-11 and C3 symmetric chiral triamide derivative (-)-12 were synthesized in high chemical yields starting from L-proline. In connection to these studies, the syntheses of the monoamide derivative (-)-14 and the C2 symmetric diamide derivative (-)-15 were achieved by using appropriate amounts of L-proline.