Literature DB >> 25307503

N-Heterocyclic carbene-catalyzed enantioselective synthesis of functionalized cyclopentenes via α,β-unsaturated acyl azoliums.

Santigopal Mondal1, Santhivardhana Reddy Yetra, Atanu Patra, Sunita S Kunte, Rajesh G Gonnade, Akkattu T Biju.   

Abstract

Highly enantioselective NHC-organocatalyzed synthesis of functionalized cyclopentenes proceeding via α,β-unsaturated acyl azolium intermediates is reported. The organocascade reaction of modified enals with malonic ester derivatives having a γ-benzoyl group involves the Michael-intramolecular aldol-β-lactonization-decarboxylation sequence to deliver cyclopentenes in good yields and excellent ee values.

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Year:  2014        PMID: 25307503     DOI: 10.1039/c4cc07433e

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


  4 in total

Review 1.  Asymmetric Organocatalysis: The Emerging Utility of α,β-Unsaturated Acylammonium Salts.

Authors:  Sreekumar Vellalath; Daniel Romo
Journal:  Angew Chem Int Ed Engl       Date:  2016-09-21       Impact factor: 15.336

Review 2.  N-Heterocyclic-Carbene-Catalyzed Domino Reactions via Two or More Activation Modes.

Authors:  Xiang-Yu Chen; Sun Li; Fabrizio Vetica; Mukesh Kumar; Dieter Enders
Journal:  iScience       Date:  2018-04-05

3.  Direct access to tetrasubstituted cyclopentenyl scaffolds through a diastereoselective isocyanide-based multicomponent reaction.

Authors:  Vitor A Fernandes; Rafaely N Lima; Yoisel B Broterson; Meire Y Kawamura; Radell Echemendía; Alexander F de la Torre; Marco A B Ferreira; Daniel G Rivera; Marcio W Paixão
Journal:  Chem Sci       Date:  2021-09-16       Impact factor: 9.825

4.  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

  4 in total

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