Asymmetric synthesis of N-aryl substituted chiral 1,4-aminoalcohol derivatives and applications in various asymmetric transformation reactions

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2007

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Odabaş, Serhat

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The asymmetric synthesis of N-aryl substituted chiral 1,4-aminoalcohols and their applications in asymmetric borane reduction and enantioselective diethylzinc addition to benzaldehyde reactions were performed starting from meso-anhydride 51 that is the cycloadduct of cyclopentadiene and maleic anhydride. The desymmetrization of meso-anhydride 51 was achieved by using quinine or quinidine with very high enantiomeric excess value (up to 98% ee) and with high chemical yield. The quinine-mediated desymmetrization of meso-anhydride 51 with methanol gave (2S,3R)-(-)-cis-monoester 52. The hemiester was subjected to chemoselective amidation with various types of N-aryl substituted amines and then, it was treated with LAH and followed by hydrogenation in the presence of palladium catalyst to get the chiral 1,4-amino alcohols. The catalytic effectiveness of these chiral 1,4-amino alcohol ligands, (2S,3R)-60, (2S,3R)-61, (2S,3R)-62 and (2S,3R)-63 were examined in asymmetric borane reduction and enantioselective diethylzinc addition to benzaldehyde reactions.

Subject Keywords

Chemistry, Organic

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http://etd.lib.metu.edu.tr/upload/12608489/index.pdf
https://hdl.handle.net/11511/16956

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Graduate School of Natural and Applied Sciences, Thesis

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Citation Formats

S. Odabaş, “Asymmetric synthesis of N-aryl substituted chiral 1,4-aminoalcohol derivatives and applications in various asymmetric transformation reactions,” M.S. - Master of Science, Middle East Technical University, 2007.