Synthesis of heterocyclic amine substituted novel 1,4-Aminoalcohols and applications in various asymmetric transformations

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Thesis Type: Postgraduate

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

Approval Date: 2007

Thesis Language: English

Student: Eda Keskin

Supervisor: CİHANGİR TANYELİ

Abstract:

Aminoalcohols are very important compounds used in various asymmetric transformations as chiral ligands or chiral auxiliaries. In this thesis, four novel heterocyclic amine substituted chiral 1,4-aminoalcohols were synthesized. In the synthetic strategy, amide esters were synthesized from (2S, 3R)-3-methoxycarbonylbicyclo[2.2.1]hept-5-ene-2-carboxylic acid by DCC coupling method. Subsequent reduction of these amide esters lead to target 1,4-aminoalcohols. The activities of these novel chiral 1,4-aminoalcohols were tested in enantioselective diethylzinc addition, Mukaiyama aldol and Diels-Alder reactions. The enantioselectivities were measured by HPLC. All the products were identified by H NMR and C NMR spectroscopy