Asymetric synthesis of 1,4-diamine based chiral ligand and organocatalyst and their applications

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2010

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Ortaylı, Oytun

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Novel 1,4-chiral diamine ligand possessing a trans-9,10-dihydro-9,10-ethanoanthracene backbone was synthesized. The synthetic plan involves first LiAlH4 reduction of the Diels-Alder adduct obtained by reaction of dimenthyl fumarate and anthracene, which is followed by reacting the corresponding alcohol and subsequent attachment of mesylate and triflate units to get good leaving groups which are available substances for introducing nitrogen units via SN2 type reactions. Consequently, by using dimesyl ester and ditriflate esters five catalysts 27, 29, 30, 33 and 38 were synthesized. The first four catalysts 27, 29, 30 and 33 were used in transfer hydrogenation reactions with transition metal whereas catalyst 38 used as an organocatalyst in direct aldol reaction between acetone and p-nitrobenzaldehyde.

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Chemistry.

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http://etd.lib.metu.edu.tr/upload/12612335/index.pdf
https://hdl.handle.net/11511/19841

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Graduate School of Natural and Applied Sciences, Thesis

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Citation Formats

O. Ortaylı, “Asymetric synthesis of 1,4-diamine based chiral ligand and organocatalyst and their applications,” M.S. - Master of Science, Middle East Technical University, 2010.