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

Authors :: Daniel Seidel
Eric G. Klauber
Chandra Kanta De
Source :: Journal of the American Chemical Society. 131:17060-17061
Publication Year :: 2009
Publisher :: American Chemical Society (ACS), 2009.
Abstract: 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.

Subjects :: Chemistry
Hydrogen bond
General Chemistry
Photochemistry
Biochemistry
Combinatorial chemistry
Catalysis
Benzoic anhydride
Kinetic resolution
chemistry.chemical_compound
Colloid and Surface Chemistry
Nucleophile
Pyridine
Pyridinium
Anion binding

Tools