Literature DB >> 21863902

Catalytic enantioselective desymmetrization of meso-diamines: a dual small-molecule catalysis approach.

Chandra Kanta De1, Daniel Seidel.   

Abstract

The desymmetrization of meso-diamines was accomplished via enantioselective monobenzoylation facilitated by the cooperative action of two small-molecule catalysts. A chiral acyl-transfer reagent is formed in situ through the interplay of benzoic anhydride, 4-(dimethylamino)pyridine as a nucleophilic catalyst, and a chiral amide-thiourea cocatalyst.

Entities:  

Year:  2011        PMID： 21863902     DOI： 10.1021/ja2060462

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


  11 in total

1.  Preparation of (-)-Nutlin-3 using enantioselective organocatalysis at decagram scale.

Authors:  Tyler A Davis; Anna E Vilgelm; Ann Richmond; Jeffrey N Johnston
Journal:  J Org Chem       Date:  2013-10-15       Impact factor: 4.354

2.  Cinchonidinium acetate as a convenient catalyst for the asymmetric synthesis of cis-stilbenediamines.

Authors:  Ryan R Walvoord; Marisa C Kozlowski
Journal:  Tetrahedron Lett       Date:  2015-06-03       Impact factor: 2.415

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.  Switchable regioselectivity in amine-catalysed asymmetric cycloadditions.

Authors:  Zhi Zhou; Zhou-Xiang Wang; Yuan-Chun Zhou; Wei Xiao; Qin Ouyang; Wei Du; Ying-Chun Chen
Journal:  Nat Chem       Date:  2017-01-16       Impact factor: 24.427

5.  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

6.  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

7.  Organocatalytic, diastereo- and enantioselective synthesis of nonsymmetric cis-stilbene diamines: a platform for the preparation of single-enantiomer cis-imidazolines for protein-protein inhibition.

Authors:  Brandon A Vara; Anand Mayasundari; John C Tellis; Michael W Danneman; Vanessa Arredondo; Tyler A Davis; Jaeki Min; Kristin Finch; R Kiplin Guy; Jeffrey N Johnston
Journal:  J Org Chem       Date:  2014-07-14       Impact factor: 4.354

Review 8.  Asymmetric ion-pairing catalysis.

Authors:  Katrien Brak; Eric N Jacobsen
Journal:  Angew Chem Int Ed Engl       Date:  2012-11-28       Impact factor: 15.336

9.  Thiourea-catalyzed enantioselective addition of indoles to pyrones: alkaloid cores with quaternary carbons.

Authors:  Charles S Yeung; Robert E Ziegler; John A Porco; Eric N Jacobsen
Journal:  J Am Chem Soc       Date:  2014-09-17       Impact factor: 15.419

10.  Enantioselective silyl protection of alcohols promoted by a combination of chiral and achiral Lewis basic catalysts.

Authors:  Nathan Manville; Hekla Alite; Fredrik Haeffner; Amir H Hoveyda; Marc L Snapper
Journal:  Nat Chem       Date:  2013-07-28       Impact factor: 24.427
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