Synthesis of a bipyridine-derived achiral thiourea trifluoromethanesulfonic acid salt and its application as an additive in organocatalytic asymmetric reactions

Date

2013-10-16

Author

Demir, Ayhan Sıtkı
BAŞÇEKEN, SİNAN

Metadata

Show full item record

This work is licensed under a Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License.

Item Usage Stats

249
views

0
downloads

The host-guest complex of a proline-thiourea bipyridine trifluoromethanesulfonic acid salt can catalyze organocatalytic asymmetric reactions such as aldol, Michael, and Mannich in polar protic medium with high stereoselectivities. The privileged bipyridine backbone and the thiourea motif are essential to the activity and enantioselectivity through hydrogen bonding interactions.

Subject Keywords

Host-guest complex, Proline-thiourea interaction, Asymmetric aldol reaction, Enantioselective Michael reaction, Asymmetric Mannich reaction

URI

https://hdl.handle.net/11511/58011

Journal

TETRAHEDRON LETTERS

DOI

https://doi.org/10.1016/j.tetlet.2013.08.004

Collections

Department of Chemistry, Article

Suggestions

OpenMETU
Core

Synthesis, characterization, and electrochromic properties of conducting copolymers of 2-[(3-thienylcarbonyl)oxy]ethyl 3-thiophene carboxylate with thiophene and pyrrole Bulut, U; Alkan, S; Yilmaz, F; Yagci, Y; Toppare, Levent Kamil (Informa UK Limited, 2004-07-01) 2-[(3-Thienylcarbonyl)oxy]ethyl 3-thiophene carboxylate (TOET) was synthesized via the reaction of 3-thionylcarboxylic acid with ethylene glycol, and electrochemically polymerized with thiophene (Th) and pyrrole (Py) by using tetrabutylannnonium tetrafluoroborate (TBAFB) as the supporting electrolyte in acetonitrile (ACN). Characterization of the resulting copolymers were performed via cyclic voltammetry, FTIR, and scanning electron microscopy (SEM). Electrical conductivities are measured by the four-probe ...
Synthesis, Characterization, and Thermal Properties of Alkyl-Functional Naphthoxazines UYAR, Tamer; Hacaloğlu, Jale; Ishida, Hatsuo (2013-02-15) A series of alkyl-functional naphthoxazine resins having various alkyl chain lengths from C1 to C18 are synthesized with a high yield and high purity by the reactions of 1,5-dihydroxynaphthalene, formaldehyde, and aliphatic amines. The proposed chemical structures of the naphthoxazines are confirmed by high-resolution mass spectrometry, H-1 nuclear magnetic resonance spectroscopy, Fourier transform infrared spectroscopy, and pyrolysis mass spectrometry studies. The alkyl-functional naphthoxazines have shown...
Synthesis of ferrocenyl pyrazoles by the reaction of 3-ferrocenylpropynal with hydrazinium salts Zora, Metin; Odabasoglu, Mustafa; Bueyuekguengoer, Orhan; Turgut, Guenseli (Elsevier BV, 2008-01-01) Synthesis of ferrocenyl-substituted pyrazoles via the reaction between 3-ferrocenylpropynal and hydrazinium salts is described. Depending upon the substitution pattern of hydrazine derivative, the reaction affords 1-alkyl/aryl-5-ferrocenylpyrazoles and/or 1-alkyl/aryl-3-ferrocenylpyrazoles. Structures of 5-ferrocenyl-1-phenyl-1H-pyrazole, 1-benzyl-5-ferrocenyl-1H-pyrazole and 2-(3-ferrocenylpyrazol-1-yl)ethanol were identified by X-ray crystallography.
Synthesis and characterization of water-soluble oligosalicylaldehyde-sulfanilic acid and its Cu(II), Co(II), Pb(II) complexes Turac, Ersen; Surme, Yavuz; Sahmetlioglu, Ertugrul; Varol, Ramazan; NARİN, Ibrahim; Toppare, Levent Kamil (2008-10-05) This work presents the synthesis and characterization of a new water-soluble oligophenol derivative, 4-(2-hydroxybenzylideneamino)benzenesulfanic acid (OSAL-SA) and its metal complexes. The chemical structure of the water-soluble polymer was characterized by nuclear magnetic resonance (H-1 NMR) and Fourier transform infrared (FTIR) spectroscopies and thermogravimetric analyses (TGAs). Pb(II), Cu(II), Co(II) complexes of the polymer were also synthesized in methanol. Characterizations of water insoluble poly...
Synthesis and biological evaluation of optically active conjugated gamma- and delta-lactone derivatives ŞARDAN, Melis; Sezer, Serdar; GUNEL, Aslihan; AKKAYA, MAHİNUR; Tanyeli, Cihangir (2012-09-15) An efficient synthesis of racemic and both enantiomeric forms of heteroaryl substituted gamma- and delta-lactone derivatives derived from allyl and homoallyl alcohol backbones has been accomplished via ring closing metathesis reaction. 2-Heteroaryl substituted allyl and homoallyl alcohols have been efficiently resolved through enzymatic method with high ee (97-99%) and known stereochemistry. Antimicrobial and antioxidant activities of target lactones were evaluated.

Citation Formats

A. S. Demir and S. BAŞÇEKEN, “Synthesis of a bipyridine-derived achiral thiourea trifluoromethanesulfonic acid salt and its application as an additive in organocatalytic asymmetric reactions,” TETRAHEDRON LETTERS, pp. 5677–5681, 2013, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/58011.