Literature DB >> 24064746

Asymmetric domino synthesis of indanes bearing four contiguous stereocentres catalyzed by sub-mol% loadings of a squaramide in minutes.

Charles C J Loh1, Daniel Hack, Dieter Enders.   

Abstract

An efficient diastereo- and enantioselective synthesis of polyfunctionalized indanes bearing four contiguous stereogenic centres in generally very short reaction times and sub-mol% squaramide catalyst loadings has been developed. The novel methodology creates a maximum of two stereocentres per bond formation via an organocatalytic Michael-Henry domino reaction.

Entities:  

Year:  2013        PMID: 24064746      PMCID: PMC4169095          DOI: 10.1039/c3cc46033a

Source DB:  PubMed          Journal:  Chem Commun (Camb)        ISSN: 1359-7345            Impact factor:   6.222


  35 in total

1.  N-heterocyclic carbene catalyzed domino reactions.

Authors:  André Grossmann; Dieter Enders
Journal:  Angew Chem Int Ed Engl       Date:  2011-11-25       Impact factor: 15.336

2.  Facile domino access to chiral bicyclo[3.2.1]octanes and discovery of a new catalytic activation mode.

Authors:  Bin Tan; Yunpeng Lu; Xiaofei Zeng; Pei Juan Chua; Guofu Zhong
Journal:  Org Lett       Date:  2010-06-18       Impact factor: 6.005

3.  Catalytic asymmetric domino Michael-Henry reaction: enantioselective access to bicycles with consecutive quaternary centers by using bifunctional catalysts.

Authors:  Magnus Rueping; Alexander Kuenkel; Roland Fröhlich
Journal:  Chemistry       Date:  2010-04-12       Impact factor: 5.236

Review 4.  Organocatalytic cascade reactions as a new tool in total synthesis.

Authors:  Christoph Grondal; Matthieu Jeanty; Dieter Enders
Journal:  Nat Chem       Date:  2010-02-19       Impact factor: 24.427

Review 5.  Asymmetric organocatalytic domino reactions.

Authors:  Dieter Enders; Christoph Grondal; Matthias R M Hüttl
Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336

6.  Water-compatible iminium activation: organocatalytic Michael reactions of carbon-centered nucleophiles with enals.

Authors:  Claudio Palomo; Aitor Landa; Antonia Mielgo; Mikel Oiarbide; Angel Puente; Silvia Vera
Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336

7.  Organocatalytic asymmetric tandem Michael-Henry reactions: a highly stereoselective synthesis of multifunctionalized cyclohexanes with two quaternary stereocenters.

Authors:  Bin Tan; Pei Juan Chua; Yongxin Li; Guofu Zhong
Journal:  Org Lett       Date:  2008-05-20       Impact factor: 6.005

8.  Assembly of spirooxindole derivatives containing four consecutive stereocenters via organocatalytic Michael-Henry cascade reactions.

Authors:  Klaus Albertshofer; Bin Tan; Carlos F Barbas
Journal:  Org Lett       Date:  2012-03-22       Impact factor: 6.005

9.  Asymmetric Michael addition of N-boc-protected oxindoles to nitroalkenes catalyzed by a chiral secondary amine.

Authors:  Chuan Wang; Xuena Yang; Dieter Enders
Journal:  Chemistry       Date:  2012-03-20       Impact factor: 5.236

10.  Diastereo- and enantioselective conjugate addition of 3-substituted oxindoles to nitroolefins catalyzed by a chiral Ni(OAc)2-diamine complex under mild conditions.

Authors:  Yan-Yan Han; Zhi-Jun Wu; Wen-Bing Chen; Xi-Lin Du; Xiao-Mei Zhang; Wei-Cheng Yuan
Journal:  Org Lett       Date:  2011-08-31       Impact factor: 6.005

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  4 in total

1.  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

2.  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

3.  Organocatalytic Asymmetric Domino Michael/Henry Reaction of Indolin-3-ones with o-Formyl-β-nitrostyrenes.

Authors:  Suruchi Mahajan; Pankaj Chauhan; Charles C J Loh; Server Uzungelis; Gerhard Raabe; Dieter Enders
Journal:  Synthesis (Stuttg)       Date:  2015-04-01       Impact factor: 3.157

4.  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

  4 in total

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