Issue 25, 2015

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

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).

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

Supplementary files

Article information

Article type
Communication
Submitted
28 ⴽⵜⵓ 2014
Accepted
21 ⵏⵓⵡ 2014
First published
01 ⴷⵓⵊ 2014

Chem. Commun., 2015,51, 5322-5325

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

M. C. Holland, J. B. Metternich, C. Mück-Lichtenfeld and R. Gilmour, Chem. Commun., 2015, 51, 5322 DOI: 10.1039/C4CC08520E

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