Synthesis of novel chiral N,N-dialkyl substituted 1,4-amino alcohols and applications in asymmetric transformation reactions

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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: Esen Çakır

Supervisor: CİHANGİR TANYELİ

Abstract:

Amino alcohols are valuable bioactive substances and frequently used as chiral catalyst in various asymmetric transformation reactions. In the synthetic route, the asymmetric synthesis of novel chiral N,N-dialkyl substituted chiral 1,4-amino alcohols are performed starting with meso-anhydride 38. Quinine-mediated desymmetrization of the anhydride with methanol afforded (2S,3R)-cis-monoester 39 with a high enantiomeric excess (up to 98% ee). Chemoselective amidation of hemiester with various N,N-dialkyl substituted amines resulted in amido esters and they were subjected to LAH reduction to afford chiral 1,4-amino alcohol ligands. The activities of the chiral ligands, (2S,3R)-43, (2S,3R)-44, (2S,3R)-45, (2S,3R)-46 were tested in various asymmetric transformation reactions, i.e. asymmetric diethylzinc addition and asymmetric Diels-Alder reactions. Keywords: 1,4-Amino alcohols, chiral ligand, asymmetric diethylzinc addition reaction, Diels-Alder reaction