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. 2015 Mar 28;51(25):5322-5.
doi: 10.1039/c4cc08520e.

Cation-π interactions in iminium ion activation: correlating quadrupole moment & enantioselectivity

M C Holland  1 , J B Metternich, C Mück-Lichtenfeld, R Gilmour
Affiliations

Cation-π interactions in iminium ion activation: correlating quadrupole moment & enantioselectivity

M C Holland et al. Chem Commun (Camb). .

Abstract

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).

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