Literature DB >> 20712303

Substituted pyrroles via olefin cross-metathesis.

Timothy J Donohoe1, Nicholas J Race, John F Bower, Cedric K A Callens.   

Abstract

Olefin cross-metathesis (CM) provides a short and convenient entry to diverse trans-γ-aminoenones. When exposed to either acid or Heck arylation conditions, these intermediates are converted to mono-, di-, or trisubstituted pyrroles. The value of this chemistry is demonstrated by its application to the tetrasubstituted pyrrole subunit of Atorvastatin.

Entities:  

Year:  2010        PMID： 20712303     DOI： 10.1021/ol101681r

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


  9 in total

1.  Scope and Mechanistic Study of the Coupling Reaction of α, β-Unsaturated Carbonyl Compounds with Alkenes: Uncovering Electronic Effects on Alkene Insertion vs Oxidative Coupling Pathways.

Authors:  Ki-Hyeok Kwon; Do W Lee; Chae S Yi
Journal:  Organometallics       Date:  2012-01-09       Impact factor: 3.876

Review 2.  Transition metal-mediated synthesis of monocyclic aromatic heterocycles.

Authors:  Anton V Gulevich; Alexander S Dudnik; Natalia Chernyak; Vladimir Gevorgyan
Journal:  Chem Rev       Date:  2013-01-10       Impact factor: 60.622

3.  A sustainable catalytic pyrrole synthesis.

Authors:  Stefan Michlik; Rhett Kempe
Journal:  Nat Chem       Date:  2013-01-20       Impact factor: 24.427

4.  Methyl 1-benzyl-5-methyl-2,4-diphenyl-1H-pyrrole-3-carboxyl-ate.

Authors:  Justin M Lopchuk; Gordon W Gribble; Jerry P Jasinski
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2014-02-22

5.  Simple two-step synthesis of 2,4-disubstituted pyrroles and 3,5-disubstituted pyrrole-2-carbonitriles from enones.

Authors:  Murat Kucukdisli; Dorota Ferenc; Marcel Heinz; Christine Wiebe; Till Opatz
Journal:  Beilstein J Org Chem       Date:  2014-02-24       Impact factor: 2.883

6.  Direct Synthesis of Highly Substituted Pyrroles and Dihydropyrroles Using Linear Selective Hydroacylation Reactions.

Authors:  Manjeet K Majhail; Paul M Ylioja; Michael C Willis
Journal:  Chemistry       Date:  2016-04-23       Impact factor: 5.236

7.  Copper-catalyzed condensation of imines and α-diazo-β-dicarbonyl compounds: modular and regiocontrolled synthesis of multisubstituted pyrroles.

Authors:  Wei Wen Tan; Naohiko Yoshikai
Journal:  Chem Sci       Date:  2015-08-03       Impact factor: 9.825

Review 8.  Beyond catalyst deactivation: cross-metathesis involving olefins containing N-heteroaromatics.

Authors:  Kevin Lafaye; Cyril Bosset; Lionel Nicolas; Amandine Guérinot; Janine Cossy
Journal:  Beilstein J Org Chem       Date:  2015-11-18       Impact factor: 2.883

9.  De novo synthesis of multisubstituted aryl amines using alkene cross metathesis.

Authors:  Matthew R Tatton; Iain Simpson; Timothy J Donohoe
Journal:  Org Lett       Date:  2014-03-19       Impact factor: 6.005
  9 in total

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