Literature DB >> 19929016

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

Chandra Kanta De1, Eric G Klauber, Daniel 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.

Entities:  

Year:  2009        PMID： 19929016     DOI： 10.1021/ja9079435

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  22 in total

1.  On- and Off-Cycle Catalyst Cooperativity in Anion-Binding Catalysis.

Authors:  David D Ford; Dan Lehnherr; C Rose Kennedy; Eric N Jacobsen
Journal:  J Am Chem Soc       Date:  2016-06-15       Impact factor: 15.419

2.  Silanediol Anion Binding and Enantioselective Catalysis.

Authors:  Jonathan W Attard; Kohei Osawa; Yong Guan; Jessica Hatt; Shin-Ichi Kondo; Anita Mattson
Journal:  Synthesis (Stuttg)       Date:  2019-03-12       Impact factor: 3.157

3.  The progression of chiral anions from concepts to applications in asymmetric catalysis.

Authors:  Robert J Phipps; Gregory L Hamilton; F Dean Toste
Journal:  Nat Chem       Date:  2012-07-24       Impact factor: 24.427

4.  Kinetic Resolution of Benzylamines via Palladium(II)-Catalyzed C-H Cross-Coupling.

Authors:  Kai-Jiong Xiao; Ling Chu; Gang Chen; Jin-Quan Yu
Journal:  J Am Chem Soc       Date:  2016-06-10       Impact factor: 15.419

5.  Enantioselective thiourea-catalyzed cationic polycyclizations.

Authors:  Robert R Knowles; Song Lin; Eric N Jacobsen
Journal:  J Am Chem Soc       Date:  2010-04-14       Impact factor: 15.419

6.  Room-temperature enantioselective C-H iodination via kinetic resolution.

Authors:  Ling Chu; Kai-Jiong Xiao; Jin-Quan Yu
Journal:  Science       Date:  2014-10-24       Impact factor: 47.728

7.  Chiral Thioureas Promote Enantioselective Pictet-Spengler Cyclization by Stabilizing Every Intermediate and Transition State in the Carboxylic Acid-Catalyzed Reaction.

Authors:  Rebekka S Klausen; C Rose Kennedy; Alan M Hyde; Eric N Jacobsen
Journal:  J Am Chem Soc       Date:  2017-08-22       Impact factor: 15.419

8.  Mechanism-Guided Development of a Highly Active Bis-thiourea Catalyst for Anion-Abstraction Catalysis.

Authors:  C Rose Kennedy; Dan Lehnherr; Naomi S Rajapaksa; David D Ford; Yongho Park; Eric N Jacobsen
Journal:  J Am Chem Soc       Date:  2016-10-11       Impact factor: 15.419

9.  Enantioselective acylation of silyl ketene acetals through fluoride anion-binding catalysis.

Authors:  James A Birrell; Jean-Nicolas Desrosiers; Eric N Jacobsen
Journal:  J Am Chem Soc       Date:  2011-08-10       Impact factor: 15.419

10.  Rhodium-catalyzed asymmetric hydrogenation of unprotected NH imines assisted by a thiourea.

Authors:  Qingyang Zhao; Jialin Wen; Renchang Tan; Kexuan Huang; Pedro Metola; Rui Wang; Eric V Anslyn; Xumu Zhang
Journal:  Angew Chem Int Ed Engl       Date:  2014-06-18       Impact factor: 15.336
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