Merging Nucleophilic and Hydrogen Bonding Catalysis: An Anion Binding Approach to the Kinetic Resolution of Amines

Merging Nucleophilic and Hydrogen Bonding Catalysis: An Anion Binding Approach to the Kinetic Resolution of Amines

A new concept for asymmetric nucleophilic catalysis is presented. Acyl pyridinium salts derived from 4-(dimethylamino)pyridine (DMAP) and benzoic anhydride are rendered chiral via interaction with a chiral thiourea anion receptor. The power of this concept is demonstrated in the context of kinetic a...

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Veröffentlicht in:Journal of the American Chemical Society 2009-12, Vol.131 (47), p.17060-17061
Hauptverfasser: De, Chandra Kanta, Klauber, Eric G, Seidel, Daniel
Format: Artikel
Sprache:eng
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Zusammenfassung:A new concept for asymmetric nucleophilic catalysis is presented. Acyl pyridinium salts derived from 4-(dimethylamino)pyridine (DMAP) and benzoic anhydride are rendered chiral via interaction with a chiral thiourea anion receptor. The power of this concept is demonstrated in the context of kinetic amine resolution.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja9079435