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    Asymmetric Henry reactions catalyzed by metal complexes of chiral oxazoline based ligands
    (Pergamon-Elsevier Science Ltd, 2013) Aydin, A. Ebru; Yuksekdanaci, Seda
    Chiral oxazolines have been synthesized from norephedrine and pyrrole nitrile or benzoyl chloride and applied to the catalytic asymmetric Henry reactions of p-nitro aldehydes with nitromethane to provide beta-hydroxy nitroalkanols in high conversion (up to 92%). The reaction was then optimized in terms of the metal, solvent, temperature, and amount of chiral ligand. The corresponding catalyst with Cu(OTf)(2) and isopropanol as the solvent gave the best enantioselectivities (up to 84% ee) of the corresponding beta-nitroalkanol for p-nitrobenzaldehyde. (C) 2012 Elsevier Ltd. All rights reserved.
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    Chiral thiourea derivatives as organocatalyts in the enantioselective Morita-Baylis-Hillman reactions
    (Arkat Usa Inc, 2020) Aydin, A. Ebru
    Novel chiral bifunctional thiourea derivatives have been synthesised and successfully applied to the intermolecular Morita-Baylis-Hillman (MBH) reaction of an aromatic aldehyde with methyl vinyl ketone (MVK) and to the intramolecular MBH reaction of omega-formyl-enone. The corresponding products were obtained with high enantioselectivities (up to 98 % ee). The thiourea organocatalyst derived from a B-amino alcohol gave high enantioselectivities (92 % ee) in the intermolecular MBH reaction, whereas the same chiral ligand afforded the corresponding product in high yield (85 %) with moderate enantioselectivity (75 % ee) in the intramolecular MBH reaction. The use of a thiophene ring-containing thiourea derivative gave high enantioselectivities in the intermolecular and intramolecular MBH reactions (85 % and 95 % ee, respectively). [GRAPHICS] .
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    Synthesis of novel ?-amino alcohols and their application in the catalytic asymmetric sulfoxidation of sulfides
    (Pergamon-Elsevier Science Ltd, 2013) Aydin, A. Ebru
    Novel chiral norephedrine-based beta-amino alcohol ligands containing a thiophene ring were prepared from norephedrine and substituted furan carbaldehydes (methyl- or ethyl-substituted) and used in combination with VO(acac)(2) for the asymmetric oxidation of aryl methyl sulfides using H2O2 as an oxidant. Amino alcohol derived Schiff bases 4,5a-b gave higher enantiomeric excesses than amino alcohol-derived reduced Schiff based ligands 6,7a-b. Of these chiral ligands, (1S,2R)-5b and (1S,2R)-7b gave high yields (90%) with moderate to high enantioselectivities (78%, 96% ee, respectively). The oxidation of other aryl methyl sulfides with (1S,2R)-5b and (1S,2R)-7b as ligands afforded the corresponding sulfoxides in 60-89% yields and with 92-99% ee. (C) 2013 Elsevier Ltd. All rights reserved.
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    Synthesis of novel thiophene-based chiral ligands and their application in asymmetric Henry reaction
    (Wiley, 2013) Aydin, A. Ebru
    Novel chiral thiolated amino alcohols were synthesized from norephedrine and thiophene carbaldehydes (methyl- or ethyl-substituted) and applied to the catalytic asymmetric Henry reaction of various aldehydes with nitromethane to provide -hydroxy nitroalkanols in high conversion (92%). The reaction was optimized in terms of the metal, solvent, temperature and amount of chiral ligand. The corresponding catalyst with Cu(OTf)2 and 2-propanol as the solvent provided the best enantioselectivities (up to 96% ee) of the corresponding nitroalcohols for aliphatic aldehydes. Copyright (c) 2013 John Wiley & Sons, Ltd.