Volume 52, Issue 2 pp. 518-533
Review

Asymmetric Counteranion-Directed Catalysis: Concept, Definition, and Applications

Manuel Mahlau

Manuel Mahlau

Max-Planck-Institut für Kohlenforschung, Kaiser-Wilhelm-Platz 1, 45470 Mülheim an der Ruhr (Germany)

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Prof. Dr. Benjamin List

Corresponding Author

Prof. Dr. Benjamin List

Max-Planck-Institut für Kohlenforschung, Kaiser-Wilhelm-Platz 1, 45470 Mülheim an der Ruhr (Germany)

Max-Planck-Institut für Kohlenforschung, Kaiser-Wilhelm-Platz 1, 45470 Mülheim an der Ruhr (Germany)Search for more papers by this author
First published: 28 November 2012
Citations: 818

Graphical Abstract

Opposites attract: This simple realization is the basis for asymmetric counteranion-directed catalysis (ACDC). All reactions proceeding via cationic intermediates are accompanied by a counteranion. Inducing high enantioselectivities in these reactions merely by ion pairing with an enantiomerically pure counteranion has been achieved for the first time during recent years.

Abstract

Recently, the use of enantiomerically pure counteranions for the induction of asymmetry in reactions proceeding through cationic intermediates has emerged as an exciting new concept, which has been termed asymmetric counteranion-directed catalysis (ACDC). Despite its success, the concept has not been fully defined and systematically discussed to date. This Review closes this gap by providing a clear definition of ACDC and by examining both clear cases as well as more ambiguous examples to illustrate the differences and overlaps with other catalysis concepts.

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