Literature DB >> 21175138

An atom-economic synthesis of nitrogen heterocycles from alkynes.

Barry M Trost1, Jean-Philip Lumb, Joseph M Azzarelli.   

Abstract

A robust route to 2,4-disubstituted pyrrole heterocycles relying upon a cascade reaction is reported. The reaction benefits from operational simplicity: it is air and moisture tolerant and is performed at ambient temperature. Control over the reaction conditions provides ready access to isopyrroles, 2,3,4-trisubstituted pyrroles, and 3-substituted pyrollidin-2-ones.

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Year:  2011        PMID： 21175138      PMCID： PMC3043142          DOI： 10.1021/ja110117g

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  14 in total

Review 1.  Cascade reactions in total synthesis.

Authors:  K C Nicolaou; David J Edmonds; Paul G Bulger
Journal:  Angew Chem Int Ed Engl       Date:  2006-11-06       Impact factor: 15.336

2.  Redox economy in organic synthesis.

Authors:  Noah Z Burns; Phil S Baran; Reinhard W Hoffmann
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

3.  Green chemistry for chemical synthesis.

Authors:  Chao-Jun Li; Barry M Trost
Journal:  Proc Natl Acad Sci U S A       Date:  2008-09-03       Impact factor: 11.205

4.  Structural diversity of organic chemistry. A scaffold analysis of the CAS Registry.

Authors:  Alan H Lipkus; Qiong Yuan; Karen A Lucas; Susan A Funk; William F Bartelt; Roger J Schenck; Anthony J Trippe
Journal:  J Org Chem       Date:  2008-05-28       Impact factor: 4.354

5.  The atom economy--a search for synthetic efficiency.

Authors:  B M Trost
Journal:  Science       Date:  1991-12-06       Impact factor: 47.728

6.  Pyrrole synthesis via allylic sp3 C-H activation of enamines followed by intermolecular coupling with unactivated alkynes.

Authors:  Souvik Rakshit; Frederic W Patureau; Frank Glorius
Journal:  J Am Chem Soc       Date:  2010-07-21       Impact factor: 15.419

7.  Rhodium(III)-catalyzed arene and alkene C-H bond functionalization leading to indoles and pyrroles.

Authors:  David R Stuart; Pamela Alsabeh; Michelle Kuhn; Keith Fagnou
Journal:  J Am Chem Soc       Date:  2010-12-06       Impact factor: 15.419

8.  Rhodium carbenoid approach for introduction of 4-substituted (Z)-pent-2-enoates into sterically encumbered pyrroles and indoles.

Authors:  Yajing Lian; Huw M L Davies
Journal:  Org Lett       Date:  2010-03-05       Impact factor: 6.005

9.  A practical method for oxazole synthesis by cycloisomerization of propargyl amides.

Authors:  Peter Wipf; Yasunori Aoyama; Tyler E Benedum
Journal:  Org Lett       Date:  2004-09-30       Impact factor: 6.005

10.  Skeletal diversity in small-molecule synthesis using ligand-controlled catalysis.

Authors:  B Lawrence Gray; Stuart L Schreiber
Journal:  J Comb Chem       Date:  2007-10-26
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  9 in total

1.  A mild and efficient AgSbF6-catalyzed synthesis of fully substituted pyrroles through a sequential propargylation/amination/cycloisomerization reaction.

Authors:  Satheesh Gujarathi; Xingui Liu; Lin Song; Howard Hendrickson; Guangrong Zheng
Journal:  Tetrahedron       Date:  2014-08-26       Impact factor: 2.457

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

Review 4.  Transition metal-catalyzed couplings of alkynes to 1,3-enynes: modern methods and synthetic applications.

Authors:  Barry M Trost; James T Masters
Journal:  Chem Soc Rev       Date:  2016-02-01       Impact factor: 54.564

5.  Multifunctionalized 3-hydroxypyrroles in a three-step, one-pot cascade process from methyl 3-TBSO-2-diazo-3-butenoate and nitrones.

Authors:  Xinfang Xu; Maxim O Ratnikov; Peter Y Zavalij; Michael P Doyle
Journal:  Org Lett       Date:  2011-10-27       Impact factor: 6.005

6.  A new strategy for the synthesis of chiral β-alkynyl esters via sequential palladium and copper catalysis.

Authors:  Barry M Trost; Benjamin R Taft; James T Masters; Jean-Philip Lumb
Journal:  J Am Chem Soc       Date:  2011-05-16       Impact factor: 15.419

Review 7.  Alkynoates as Versatile and Powerful Chemical Tools for the Rapid Assembly of Diverse Heterocycles under Transition-Metal Catalysis: Recent Developments and Challenges.

Authors:  Imtiaz Khan; Aliya Ibrar; Sumera Zaib
Journal:  Top Curr Chem (Cham)       Date:  2021-01-05

8.  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

9.  Asymmetric synthesis of chiral β-alkynyl carbonyl and sulfonyl derivatives via sequential palladium and copper catalysis.

Authors:  Barry M Trost; James T Masters; Benjamin R Taft; Jean-Philip Lumb
Journal:  Chem Sci       Date:  2016-06-10       Impact factor: 9.825
  9 in total

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