Literature DB >> 24729588

N-heterocyclic carbene-catalyzed enantioselective annulation of indolin-3-ones with bromoenals.

Qijian Ni1, Xiaoxiao Song, Gerhard Raabe, Dieter Enders.   

Abstract

N-Heterocyclic carbene-catalyzed reactions of indolin-3-ones with 2-bromoenals opened an asymmetric access to 3,4-dihydropyrano[3,2-b]indol-2(5 H)-ones in good yields and with good to excellent enantioselectivities. This protocol tolerates a broad substrate scope. In addition, a possible mechanism for the annulation reaction is presented.
© 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  N-heterocyclic carbenes; annulation; asymmetric synthesis; dihydropyranoindol-2-ones; organocatalysis

Year:  2014        PMID： 24729588     DOI： 10.1002/asia.201402052

Source DB:  PubMed          Journal:  Chem Asian J        ISSN： 1861-471X


  6 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.  N-Heterocyclic Carbene Catalyzed Enantioselective Annulation of Benzothiazolyl Ethyl Acetates with 2-Bromoenals.

Authors:  Qijian Ni; Jiawen Xiong; Xiaoxiao Song; Gerhard Raabe; Dieter Enders
Journal:  Synlett       Date:  2015-06-11       Impact factor: 2.454

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.  N-Heterocyclic carbene-catalyzed oxidative [3 + 2] annulation of dioxindoles and enals: cross coupling of homoenolate and enolate.

Authors:  Xiang-Yu Chen; Kun-Quan Chen; De-Qun Sun; Song Ye
Journal:  Chem Sci       Date:  2016-11-09       Impact factor: 9.825

5.  A solid-supported organocatalyst for asymmetric Mannich reaction to construct C2-quaternary indolin-3-ones.

Authors:  Jian-Xiong An; Fen-Fen Yang; Pan Wang; Zhi-Cheng Gu; Yan Li; Lei Chen; Yong-Long Zhao; Bin He
Journal:  RSC Adv       Date:  2022-03-02       Impact factor: 3.361

6.  Enantioselective annulation of enals with 2-naphthols by triazolium salts derived from l-phenylalanine.

Authors:  Guo-Tai Li; Qing Gu; Shu-Li You
Journal:  Chem Sci       Date:  2015-04-30       Impact factor: 9.825
  6 in total

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