Issue 25, 2015
From the journal:

Chemical Communications

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

M. C. Holland,a   J. B. Metternich,a   C. Mück-Lichtenfelda  and  R. Gilmour*ab  

* Corresponding authors

a Organisch Chemisches Institut, and Excellence Cluster EXC 1003, Cells in Motion, Westfälische Wilhelms-Universität Münster, Corrensstrasse 40, Münster, Germany
E-mail: ryan.gilmour@uni-muenster.de

b Excellence Cluster EXC 1003, Cells in Motion, Westfälische Wilhelms-Universität Münster, Münster, Germany

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

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Article information

DOI
https://doi.org/10.1039/C4CC08520E
Article type
Communication
Submitted
28 ⴽⵜⵓ 2014
Accepted
21 ⵏⵓⵡ 2014
First published
01 ⴷⵓⵊ 2014

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

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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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