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Here, we study the Diels\u2010Alder reaction of 2\u2032\u2010hydroxychalcones, as dienophiles, with two dienes, catalyzed by chiral organo\u2010boron Lewis acid complexes. We theoretically evaluate the mechanism that has been empirically proposed in the literature, and we clarify several results that didn't allow the full rationalization of the experimental data. Therefore, we show that similar ligands in the complexes lead to quite different enantioselectivities, due to different steric interactions with the attacking diene. 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