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

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2007
Çakır, Esen
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

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Citation Formats
E. Çakır, “Synthesis of novel chiral N,N-dialkyl substituted 1,4-amino alcohols and applications in asymmetric transformation reactions,” M.S. - Master of Science, Middle East Technical University, 2007.