Literature DB >> 18393508

Brønsted-acid-catalyzed activation of nitroalkanes: a direct enantioselective aza-Henry reaction.

Magnus Rueping1, Andrey P Antonchick.   

Abstract

A direct asymmetric organocatalytic aza-Henry reaction has been developed in which a new bifunctional Brønsted-acid-catalyzed activation of nitroalkanes provides an efficient access to alpha,beta-diamino acids with high dia- and enantioselectivities under mild and base-free reaction conditions.

Entities:  

Year:  2008        PMID： 18393508     DOI： 10.1021/ol8003589

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


  13 in total

1.  Catalytic, Enantioselective Synthesis of Stilbene cis-Diamines: A Concise Preparation of (-)-Nutlin-3, a Potent p53/MDM2 Inhibitor.

Authors:  Tyler A Davis; Jeffrey N Johnston
Journal:  Chem Sci       Date:  2011-03-25       Impact factor: 9.825

2.  Enantioselective Addition of Bromonitromethane to Aliphatic N-Boc Aldimines Using a Homogeneous Bifunctional Chiral Organocatalyst.

Authors:  Kenneth E Schwieter; Jeffrey N Johnston
Journal:  ACS Catal       Date:  2015       Impact factor: 13.084

3.  Chiral proton catalysis of secondary nitroalkane additions to azomethine: synthesis of a potent GlyT1 inhibitor.

Authors:  Tyler A Davis; Michael W Danneman; Jeffrey N Johnston
Journal:  Chem Commun (Camb)       Date:  2012-04-30       Impact factor: 6.222

4.  Bifunctional asymmetric catalysis: amplification of Brønsted basicity can orthogonally increase the reactivity of a chiral Brønsted acid.

Authors:  Tyler A Davis; Jeremy C Wilt; Jeffrey N Johnston
Journal:  J Am Chem Soc       Date:  2010-03-10       Impact factor: 15.419

5.  Organocatalytic, enantioselective synthesis of VNI: a robust therapeutic development platform for Chagas, a neglected tropical disease.

Authors:  Mark C Dobish; Fernando Villalta; Michael R Waterman; Galina I Lepesheva; Jeffrey N Johnston
Journal:  Org Lett       Date:  2012-12-07       Impact factor: 6.005

6.  Development of an Intermittent-Flow Enantioselective Aza-Henry Reaction Using an Arylnitromethane and Homogeneous Brønsted Acid-Base Catalyst with Recycle.

Authors:  Sergey V Tsukanov; Martin D Johnson; Scott A May; Morgan Rosemeyer; Michael A Watkins; Stanley P Kolis; Matthew H Yates; Jeffrey N Johnston
Journal:  Org Process Res Dev       Date:  2016-02-01       Impact factor: 3.317

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

8.  Preparation of H,(4) PyrrolidineQuin-BAM (PBAM).

Authors:  Tyler A Davis; Mark C Dobish; Kenneth E Schwieter; Aspen C Chun; Jeffrey N Johnston
Journal:  Organic Synth       Date:  2012-02-22

9.  Highly enantioselective hydrogenation of enamides catalyzed by chiral phosphoric acids.

Authors:  Guilong Li; Jon C Antilla
Journal:  Org Lett       Date:  2009-03-05       Impact factor: 6.005

10.  One-Pot Asymmetric Nitro-Mannich/Hydroamination Cascades for the Synthesis of Pyrrolidine Derivatives: Combining Organocatalysis and Gold Catalysis.

Authors:  David M Barber; Andrej Duriš; Amber L Thompson; Hitesh J Sanganee; Darren J Dixon
Journal:  ACS Catal       Date:  2014-01-06       Impact factor: 13.084
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