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Abstract | Cited by

A linear correlation between quadrupole moment (Qzz) and enantioselectivity (es) advocates the notion that a cation–π interaction is a contributing factor in the addition of uncharged nucleophiles to iminium salts derived from MacMillan's 1st generation catalyst. The quadrupole moment of the aryl shielding group is a useful qualitative parameter for predicting selectivity (Qzz < 0 → high es).

Graphical abstract: Cation–π interactions in iminium ion activation: correlating quadrupole moment & enantioselectivity

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