305791-50-8Relevant academic research and scientific papers
Ion-pairing catalysis in the enantioselective addition of hydrazones to N-acyldihydropyrrole derivatives
Zabaleta, Nagore,Uria, Uxue,Reyes, Efraim,Carrillo, Luisa,Vicario, Jose L.
supporting information, p. 8905 - 8908 (2018/08/17)
We have demonstrated that dihydropyrrole-based enamide derivatives can act as efficient precursors of chiral quaternary N-acyliminium salts under Br?nsted acid catalysis that undergo reactions with hydrazones, the latter participating as masked nucleophilic carbonyl group equivalents. The optimized methodology provides a variety of enantiopure α-substituted proline derivatives in excellent yields, being even compatible with disubstituted β-enamides that generate two contiguous stereocentres.
Chiral phosphoric acid-catalyzed enantioselective three-component Povarov reaction using cyclic enethioureas as dienophiles: Stereocontrolled access to enantioenriched hexahydropyrroloquinolines
Dagousset, Guillaume,Retailleau, Pascal,Masson, Geraldine,Zhu, Jieping
experimental part, p. 5869 - 5873 (2012/06/18)
Three become one: Phosphoric acid-catalyzed enantioselective three-component Povarov reactions of aldehydes, anilines, and endocyclic enethioureas have been developed (see scheme). This process afforded hexahydropyrroloquinolines in high yields with excellent diastereo- and enantioselectivities. The presence of the thiourea functionality is crucial for the enantioselectivity of the reaction. Copyright
Multi-component coupling reactions: Synthesis of a guanidine containing analog of the hexahydropyrrolo[3,2-c]quinoline alkaloid martinelline
Batey,Powell
, p. 2362 - 2363 (2007/10/03)
A multi-component coupling reaction is used to synthesize a highly functionalized guanidine containing pyrroloquinoline analog of martinelline that displays bradykinin B2 receptor antagonist activity.
A general synthetic method for the formation of substituted 5-aminotetrazoles from thioureas: a strategy for diversity amplification.
Batey,Powell
, p. 3237 - 3240 (2007/10/03)
A general method for the synthesis of 5-aminotetrazoles is outlined using the mercury(II)-promoted attack of azide anion on a thiourea. The reaction proceeds through a guanyl azide intermediate, which undergoes electrocyclization to the tetrazole. The method is high yielding and provides access to mono-, di-, and trisubstituted 5-aminotetrazoles, targets of potential interest for combinatorial library development.
