Literature DB >> 20359172

Enantioselective alpha-amination of 1,3-dicarbonyl compounds using squaramide derivatives as hydrogen bonding catalysts.

Hideyuki Konishi1, Tin Yiu Lam, Jeremiah P Malerich, Viresh H Rawal.   

Abstract

Catalytic enantioselective alpha-hydrazination of 1,3-dicarbonyl compounds with azodicarboxylates was investigated in the presence of our newly developed hydrogen bonding catalyst, squaramide 3j. High yields and high enantioselectivities were achieved with low catalyst loading under mild conditions.

Entities:  

Year:  2010        PMID： 20359172      PMCID： PMC2862278          DOI： 10.1021/ol1005104

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  35 in total

1.  Catalytic, highly enantioselective, direct amination of beta-ketoesters.

Authors:  Mauro Marigo; Karsten Juhl; Karl Anker Jørgensen
Journal:  Angew Chem Int Ed Engl       Date:  2003-03-28       Impact factor: 15.336

Review 2.  Recent advances in catalytic, enantioselective alpha aminations and alpha oxygenations of carbonyl compounds.

Authors:  Jacob M Janey
Journal:  Angew Chem Int Ed Engl       Date:  2005-07-11       Impact factor: 15.336

3.  Theoretical studies on the bifunctionality of chiral thiourea-based organocatalysts: competing routes to C-C bond formation.

Authors:  Andrea Hamza; Gabor Schubert; Tibor Soós; Imre Papai
Journal:  J Am Chem Soc       Date:  2006-10-11       Impact factor: 15.419

4.  Enantio- and diastereoselective Michael reaction of 1,3-dicarbonyl compounds to nitroolefins catalyzed by a bifunctional thiourea.

Authors:  Tomotaka Okino; Yasutaka Hoashi; Tomihiro Furukawa; Xuenong Xu; Yoshiji Takemoto
Journal:  J Am Chem Soc       Date:  2005-01-12       Impact factor: 15.419

5.  Recent Progress on the Stereoselective Synthesis of Cyclic Quaternary alpha-Amino Acids.

Authors:  Carlos Cativiela; Mario Ordóñez
Journal:  Tetrahedron Asymmetry       Date:  2009-01-30

6.  Highly enantioselective electrophilic amination and michael addition of cyclic beta-ketoesters induced by lanthanides and (S,S)-ip-pybox: the mechanism.

Authors:  Josep Comelles; Alex Pericas; Marcial Moreno-Mañas; Adelina Vallribera; Galí Drudis-Solé; Agusti Lledos; Teodor Parella; Anna Roglans; Santiago García-Granda; Laura Roces-Fernández
Journal:  J Org Chem       Date:  2007-02-22       Impact factor: 4.354

7.  Catalytic asymmetric direct alpha-amination reactions of 2-keto esters: a simple synthetic approach to optically active syn-beta-amino-alpha-hydroxy esters.

Authors:  Karsten Juhl; Karl Anker Jørgensen
Journal:  J Am Chem Soc       Date:  2002-03-20       Impact factor: 15.419

8.  Highly enantioselective amination of alpha-substituted alpha-cyanoacetates with chiral catalysts accessible from both quinine and quinidine.

Authors:  Xiaofeng Liu; Hongming Li; Li Deng
Journal:  Org Lett       Date:  2005-01-20       Impact factor: 6.005

9.  An improved lanthanum catalyst system for asymmetric amination: toward a practical asymmetric synthesis of AS-3201 (Ranirestat).

Authors:  Tomoyuki Mashiko; Naoya Kumagai; Masakatsu Shibasaki
Journal:  Org Lett       Date:  2008-06-04       Impact factor: 6.005

10.  Chiral squaramide derivatives are excellent hydrogen bond donor catalysts.

Authors:  Jeremiah P Malerich; Koji Hagihara; Viresh H Rawal
Journal:  J Am Chem Soc       Date:  2008-10-11       Impact factor: 15.419
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  17 in total

1.  A Nucleophilic Strategy for Enantioselective Intermolecular α-Amination: Access to Enantioenriched α-Arylamino Ketones.

Authors:  Dillon H Miles; Joan Guasch; F Dean Toste
Journal:  J Am Chem Soc       Date:  2015-06-12       Impact factor: 15.419

2.  Mannich-type Reactions of Cyclic Nitrones: Effective Methods for the Enantioselective Synthesis of Piperidine-containing Alkaloids.

Authors:  Vladislav G Lisnyak; Tessa Lynch-Colameta; Scott A Snyder
Journal:  Angew Chem Int Ed Engl       Date:  2018-10-19       Impact factor: 15.336

3.  Exploring the potential of diarylacetylenediols as hydrogen bonding catalysts.

Authors:  Yunus E Türkmen; Viresh H Rawal
Journal:  J Org Chem       Date:  2013-08-14       Impact factor: 4.354

4.  Enantioselective direct α-amination of aldehydes via a photoredox mechanism: a strategy for asymmetric amine fragment coupling.

Authors:  Giuseppe Cecere; Christian M König; Jennifer L Alleva; David W C MacMillan
Journal:  J Am Chem Soc       Date:  2013-07-26       Impact factor: 15.419

5.  Quantification of electrophilic activation by hydrogen-bonding organocatalysts.

Authors:  Ryan R Walvoord; Phuong N H Huynh; Marisa C Kozlowski
Journal:  J Am Chem Soc       Date:  2014-11-04       Impact factor: 15.419

6.  Enantioselective selenocyclization via dynamic kinetic resolution of seleniranium ions by hydrogen-bond donor catalysts.

Authors:  Hu Zhang; Song Lin; Eric N Jacobsen
Journal:  J Am Chem Soc       Date:  2014-11-12       Impact factor: 15.419

7.  Cobalt(III) Werner Complexes with 1,2-Diphenylethylenediamine Ligands: Readily Available, Inexpensive, and Modular Chiral Hydrogen Bond Donor Catalysts for Enantioselective Organic Synthesis.

Authors:  Kyle G Lewis; Subrata K Ghosh; Nattamai Bhuvanesh; John A Gladysz
Journal:  ACS Cent Sci       Date:  2015-03-23       Impact factor: 14.553

8.  Squaramide-catalyzed enantioselective Michael addition of masked acyl cyanides to substituted enones.

Authors:  Kin S Yang; Antoinette E Nibbs; Yunus E Türkmen; Viresh H Rawal
Journal:  J Am Chem Soc       Date:  2013-10-17       Impact factor: 15.419

9.  Enantioselective α-Amination Enabled by a BINAM-Derived Phase-Transfer Catalyst.

Authors:  H M Nelson; J S Patel; H P Shunatona; F D Toste
Journal:  Chem Sci       Date:  2015-01-01       Impact factor: 9.825

10.  Asymmetric α-amination of β-keto esters using a guanidine-bisurea bifunctional organocatalyst.

Authors:  Minami Odagi; Yoshiharu Yamamoto; Kazuo Nagasawa
Journal:  Beilstein J Org Chem       Date:  2016-02-04       Impact factor: 2.883
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