Merging nucleophilic and hydrogen bonding catalysis: an anion binding approach to the kinetic resolution of amines

Journal of the American Chemical Society
Chandra Kanta DeDaniel Seidel

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.

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Citations

Jun 24, 2010·Journal of the American Chemical Society·Adam R BrownEric N Jacobsen
Aug 2, 2011·Journal of the American Chemical Society·James A BirrellEric N Jacobsen
Aug 26, 2011·Journal of the American Chemical Society·Chandra Kanta De, Daniel Seidel
Feb 18, 2010·Journal of the American Chemical Society·Brandon S FowlerScott J Miller
Jun 11, 2011·The Journal of Organic Chemistry·Suzanne M OpalkaD Tyler McQuade
Jan 31, 2012·The Journal of Organic Chemistry·Chandra Bhushan Tripathi, Santanu Mukherjee
Apr 12, 2011·Organic Letters·Eric G KlauberDaniel Seidel
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Feb 6, 2016·Journal of the American Chemical Society·Shunxi DongCarsten Bolm
Jun 2, 2016·Journal of the American Chemical Society·Kai-Jiong XiaoJin-Quan Yu
Jun 9, 2016·Journal of the American Chemical Society·David D FordEric N Jacobsen
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Aug 31, 2010·Angewandte Chemie·Gemma E Veitch, Eric N Jacobsen

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