Literature DB >> 24734923

Organocatalytic asymmetric Michael-Michael cascade for the construction of highly functionalized N-fused piperidinoindoline derivatives.

Yong-Long Zhao1, Yao Wang, Jian Cao, Yong-Min Liang, Peng-Fei Xu.   

Abstract

Application of indolin-3-one derivatives in a cascade reaction for efficient assembly of complex molecules is a much less explored research area. It is demonstrated that structurally interesting polysubstituted piperidino[1,2-a]indoline compounds containing four contiguous stereocenters including one tetrasubstituted carbon center can be readily obtained with good yields (up to 94% yield) and excellent enantioselectivities (up to >99% ee) by employing indolin-3-one derivatives as substrates via bifunctional catalysis.

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Year:  2014        PMID: 24734923     DOI: 10.1021/ol5008185

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


  7 in total

1.  Asymmetric synthesis of 1H-pyrrol-3(2H)-ones from 2,3-diketoesters by combination of aldol condensation with benzilic acid rearrangement.

Authors:  Qiang Sha; Hadi Arman; Michael P Doyle
Journal:  Chem Commun (Camb)       Date:  2016-01-04       Impact factor: 6.222

2.  Palladium-catalyzed direct C(sp3)-H arylation of indole-3-ones with aryl halides: a novel and efficient method for the synthesis of nucleophilic 2-monoarylated indole-3-ones.

Authors:  Yong-Long Zhao; Yong-Qin Tang; Xing-Hai Fei; Tao Xiao; Ya-Dong Lu; Xiao-Zhong Fu; Bin He; Meng Zhou; Chun Li; Peng-Fei Xu; Yuan-Yong Yang
Journal:  RSC Adv       Date:  2018-07-16       Impact factor: 3.361

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.  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

5.  Synthesis of tetracyclic indolin-3-ones through Pd-catalyzed intramolecular deacetylative dearomatization of 3-acetoxy-indoles.

Authors:  Ren-Xiao Liang; Ke Wang; Ling-Jie Song; Wei-Jian Sheng; Yi-Xia Jia
Journal:  RSC Adv       Date:  2019-05-07       Impact factor: 3.361

6.  A quadruple cascade protocol for the one-pot synthesis of fully-substituted hexahydroisoindolinones from simple substrates.

Authors:  Hong-Bo Zhang; Yong-Chun Luo; Xiu-Qin Hu; Yong-Min Liang; Peng-Fei Xu
Journal:  Beilstein J Org Chem       Date:  2016-02-11       Impact factor: 2.883

7.  Oxidative Dearomative Cross-Dehydrogenative Coupling of Indoles with Diverse C-H Nucleophiles: Efficient Approach to 2,2-Disubstituted Indolin-3-ones.

Authors:  Xue Yan; Ying-De Tang; Cheng-Shi Jiang; Xigong Liu; Hua Zhang
Journal:  Molecules       Date:  2020-01-20       Impact factor: 4.411

  7 in total

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