Abstract
A 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.
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