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

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 essenti...

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Veröffentlicht in:	Tetrahedron letters 2013-10, Vol.54 (42), p.5677-5681
Hauptverfasser:	Demir, Ayhan Sıtkı, Basceken, Sinan
Format:	Artikel
Sprache:	eng
Schlagworte:	Additives Asymmetric aldol reaction Asymmetric Mannich reaction Asymmetry Backbone Enantioselective Michael reaction Host–guest complex Hydrogen bonding Proline–thiourea interaction Stereoselectivity Synthesis (chemistry) Tetrahedrons Thioureas
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Beschreibung
Zusammenfassung:	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.
ISSN:	0040-4039 1873-3581
DOI:	10.1016/j.tetlet.2013.08.004