Literature DB >> 24492969

N-heterocyclic carbene catalyzed activation of esters: a new option for asymmetric domino reactions.

Pankaj Chauhan1, Dieter Enders.   

Abstract

Esters-what else! A new strategy in NHC organocatalysis allows the α-, β- and γ-activation of saturated and unsaturated esters. The resulting acyl azolium intermediates efficiently participate in domino reactions with suitable substrates to generate synthetically valuable carbo- and heterocycles with very good diastereo- and excellent enantioselectivities.
Copyright © 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  N-heterocyclic carbenes; asymmetric synthesis; domino reactions; esters; organocatalysis

Year:  2014        PMID： 24492969     DOI： 10.1002/anie.201309952

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN： 1433-7851            Impact factor:   15.336


  17 in total

Review 1.  Organocatalytic Reactions Enabled by N-Heterocyclic Carbenes.

Authors:  Darrin M Flanigan; Fedor Romanov-Michailidis; Nicholas A White; Tomislav Rovis
Journal:  Chem Rev       Date:  2015-05-20       Impact factor: 60.622

2.  Theoretical study of the mechanism of the N-heterocyclic carbene-catalyzed cyclotetramerization of acrylates.

Authors:  Dehui Chang; Qiaoqiao Yang; Meng Li; Ran Fang
Journal:  J Mol Model       Date:  2015-12-22       Impact factor: 1.810

3.  Streocontrolled construction of six vicinal stereogenic centers on spiropyrazolones via organocascade Michael/Michael/1,2-addition reactions.

Authors:  Pankaj Chauhan; Suruchi Mahajan; Charles C J Loh; Gerhard Raabe; Dieter Enders
Journal:  Org Lett       Date:  2014-05-19       Impact factor: 6.005

4.  NHC-Catalyzed Asymmetric Synthesis of Functionalized Succinimides from Enals and α-Ketoamides.

Authors:  Lei Wang; Qijian Ni; Marcus Blümel; Tao Shu; Gerhard Raabe; Dieter Enders
Journal:  Chemistry       Date:  2015-04-15       Impact factor: 5.236

5.  Asymmetric synthesis of tetrahydropyridines via an organocatalytic one-pot multicomponent Michael/aza-Henry/cyclization triple domino reaction.

Authors:  Marcus Blümel; Pankaj Chauhan; Robert Hahn; Gerhard Raabe; Dieter Enders
Journal:  Org Lett       Date:  2014-11-07       Impact factor: 6.005

6.  Carbon-carbon bond activation of cyclobutenones enabled by the addition of chiral organocatalyst to ketone.

Authors:  Bao-Sheng Li; Yuhuang Wang; Zhichao Jin; Pengcheng Zheng; Rakesh Ganguly; Yonggui Robin Chi
Journal:  Nat Commun       Date:  2015-02-05       Impact factor: 14.919

7.  Asymmetric synthesis of functionalized cyclohexanes bearing five stereocenters via a one-pot organocatalytic Michael-Michael-1,2-addition sequence.

Authors:  Pankaj Chauhan; Gregor Urbanietz; Gerhard Raabe; Dieter Enders
Journal:  Chem Commun (Camb)       Date:  2014-07-04       Impact factor: 6.222

8.  Organocatalytic Asymmetric Synthesis of Dihydroisoquinolinones via a One-Pot Aza-Henry-Hemiaminalization-Oxidation Sequence.

Authors:  Robert Hahn; Ehsan Jafari; Gerhard Raabe; Dieter Enders
Journal:  Synthesis (Stuttg)       Date:  2015-02-01       Impact factor: 3.157

9.  Asymmetric synthesis of highly functionalized tetrahydropyrans via a one-pot organocatalytic Michael/Henry/ketalization sequence.

Authors:  Robert Hahn; Gerhard Raabe; Dieter Enders
Journal:  Org Lett       Date:  2014-06-27       Impact factor: 6.005

10.  Isothiourea-catalysed enantioselective Michael addition of N-heterocyclic pronucleophiles to α,β-unsaturated aryl esters.

Authors:  Chang Shu; Honglei Liu; Alexandra M Z Slawin; Cameron Carpenter-Warren; Andrew D Smith
Journal:  Chem Sci       Date:  2019-10-23       Impact factor: 9.825
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