Asymmetric synthesis of chiral camphor fused pyridine type novel organocatalysts


Thesis Type: Postgraduate

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

Approval Date: 2009

Thesis Language: English

Student: Murat Küçükdişli

Supervisor: CİHANGİR TANYELİ

Abstract:

Chiral pyridines as organocatalysts have been used in asymmetric organic synthesis in recent years. The asymmetric synthesis of camphor fused pyridine type novel organocatalysts were perfomed starting from cheap and easily available natural (+)-camphor. Using camphor fused pyridine skeleton, six organocatalysts 29, 32, 33, 38, 40, and 41were successfully synthesized. The first four nucleophilic and Lewis base catalysts 29, 32, and 33 are different P-oxides and P,N-dioxides which were tested in allylation of aldehydes via allyltrichlorosilane. L-proline amide 38 and D-proline amide 40 can be named as secondary amine catalyst. They were tested in direct aldol reaction between acetone and aromatic aldehydes in aqueous medium. Final group of catalyst is hydrogen bonding type catalyst which is thiourea based 41.