Literature DB >> 24346939

Asymmetric synthesis of pyrroloindolones by N-heterocyclic carbene catalyzed [2+3] annulation of α-chloroaldehydes with nitrovinylindoles.

Qijian Ni1, Huan Zhang, André Grossmann, Charles C J Loh, Carina Merkens, Dieter Enders.   

Abstract

NHC-enolate plus 3: N-heterocyclic carbenes (NHCs) serve as organocatalysts for the [2+3] annulation of nitrovinylindoles with α-chloroaldehydes via an intermediate azolium enolate. The method provides trans-disubstituted pyrroloindolones with good yields and excellent diastereo- and enantioselectivities. Further transformations lead to tetracyclic pyrrolo[1,2-a]indoles with potential psychotropic and other bioactivities.
Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  N-heterocyclic carbenes; annulation; asymmetric synthesis; indole derivatives; organocatalysis

Year:  2013        PMID： 24346939     DOI： 10.1002/anie.201305957

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


  9 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.  Switchable selectivity in an NHC-catalysed dearomatizing annulation reaction.

Authors:  Chang Guo; Mirco Fleige; Daniel Janssen-Müller; Constantin G Daniliuc; Frank Glorius
Journal:  Nat Chem       Date:  2015-08-31       Impact factor: 24.427

3.  Regio- and stereoselective synthesis of benzothiazolo-pyrimidinones via an NHC-catalyzed Mannich/lactamization domino reaction.

Authors:  Qijian Ni; Xiaoxiao Song; Jiawen Xiong; Gerhard Raabe; Dieter Enders
Journal:  Chem Commun (Camb)       Date:  2015-01-25       Impact factor: 6.222

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 N-Heterocyclic Carbene Catalyzed Annulation of 2-Alkenylbenzothiazoles with α-Chloro Aldehydes.

Authors:  Xiaoxiao Song; Qijian Ni; Chen Zhu; Gerhard Raabe; Dieter Enders
Journal:  Synthesis (Stuttg)       Date:  2014-11-06       Impact factor: 3.157

6.  Asymmetric synthesis of cyclopentanes bearing four contiguous stereocenters via an NHC-catalyzed Michael/Michael/esterification domino reaction.

Authors:  Tao Shu; Qijian Ni; Xiaoxiao Song; Kun Zhao; Tianyu Wu; Rakesh Puttreddy; Kari Rissanen; Dieter Enders
Journal:  Chem Commun (Camb)       Date:  2016-01-11       Impact factor: 6.222

7.  A tandem dearomatization/rearomatization strategy: enantioselective N-heterocyclic carbene-catalyzed α-arylation.

Authors:  Zijun Wu; Jian Wang
Journal:  Chem Sci       Date:  2018-12-27       Impact factor: 9.825

8.  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

9.  Asymmetric synthesis of N-bridged [3.3.1] ring systems by phosphonium salt/Lewis acid relay catalysis.

Authors:  Jian-Ping Tan; Kehan Li; Boming Shen; Cheng Zhuang; Zanjiao Liu; Kai Xiao; Peiyuan Yu; Bing Yi; Xiaoyu Ren; Tianli Wang
Journal:  Nat Commun       Date:  2022-01-18       Impact factor: 14.919
  9 in total

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