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

Demir, Ayhan Sıtkı
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.


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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 ...
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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: