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Trifunctional squaramide catalyst for efficient enantioselective Henry reaction activation

AutorAlegre-Requena, Juan V. ; Marqués-López, Eugenia ; Herrera, Raquel P.
Palabras claveOrganocatalysis
Nitroalkanes
Trifunctional catalysts
Squaramides
Henry reaction
Aldehydes
Fecha de publicación2016
EditorWiley-VCH
CitaciónAdvanced Synthesis and Catalysis 358(11): 1801-1809 (2016)
ResumenA new class of trifunctional squaramide catalyst acting by means of multiple interactions has been found in a study of the Henry reaction. Enantiomerically enriched nitroaldol products were obtained in good yields and high enantioselectivities under mild conditions using one of the smallest amounts of organocatalyst reported so far for this reaction (0.25 mol%). The catalyst was able to generate hydrogen bonding and anion-π/hydrogen-π interactions with the substrates, responsible of the improvement in the reactivity and the enantioselectivity of this process. Computational calculations support a mechanistic hypothesis based on an anion-π effect, this being the first example reported in asymmetric catalysis.
URIhttp://hdl.handle.net/10261/155750
DOI10.1002/adsc.201600046
Identificadoresdoi: 10.1002/adsc.201600046
e-issn: 1615-4169
issn: 1615-4150
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