Literature DB >> 18841992

Lewis acid catalyzed [1,3]-sigmatropic rearrangement of vinyl aziridines.

Matthew Brichacek1, Dongeun Lee, Jon T Njardarson.   

Abstract

This paper details the copper-catalyzed ring expansion of vinyl aziridines to 3-pyrrolines. Broad substrate scope (24 examples) using tosyl- and phthalimide-protected vinyl aziridine substrates is observed. Cu(hfacac)2 was determined to be superior to all other catalysts tested.

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Year:  2008        PMID： 18841992      PMCID： PMC2646081          DOI： 10.1021/ol802123e

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


  12 in total

1.  Birch Reduction of Electron-Deficient Pyrroles.

Authors:  Timothy J. Donohoe; Paul M. Guyo
Journal:  J Org Chem       Date:  1996-11-01       Impact factor: 4.354

2.  Intramolecular dipolar cycloaddition reactions of azomethine ylides.

Authors:  Iain Coldham; Richard Hufton
Journal:  Chem Rev       Date:  2005-07       Impact factor: 60.622

3.  Construction of enantiopure pyrrolidine ring system via asymmetric [3+2]-cycloaddition of azomethine ylides.

Authors:  Ganesh Pandey; Prabal Banerjee; Smita R Gadre
Journal:  Chem Rev       Date:  2006-11       Impact factor: 60.622

4.  Highly selective copper-catalyzed ring expansion of vinyl thiiranes: application to synthesis of biotin and the heterocyclic core of plavix.

Authors:  Erik Rogers; Hiroshi Araki; Lindsay A Batory; Christine E McInnis; Jon T Njardarson
Journal:  J Am Chem Soc       Date:  2007-02-16       Impact factor: 15.419

5.  Practical olefin aziridination with a broad substrate scope.

Authors:  Tung Siu; Andrei K Yudin
Journal:  J Am Chem Soc       Date:  2002-01-30       Impact factor: 15.419

Review 6.  Naturally occurring proline analogues.

Authors:  A B Mauger
Journal:  J Nat Prod       Date:  1996-12       Impact factor: 4.050

Review 7.  2,3-dichloro-5,6-dicyanobenzoquinone and its reactions.

Authors:  D Walker; J D Hiebert
Journal:  Chem Rev       Date:  1967-04       Impact factor: 60.622

8.  Design and synthesis of a 3,4-dehydroproline amide discovery library.

Authors:  Stefan Werner; Dhanalakshmi Kasi; Kay M Brummond
Journal:  J Comb Chem       Date:  2007-06-14

Review 9.  Cancer chemotherapy and heterocyclic compounds.

Authors:  M Kidwai; R Venkataramanan; R Mohan; P Sapra
Journal:  Curr Med Chem       Date:  2002-06       Impact factor: 4.530

10.  Stereoselective Synthesis of Quaternary Proline Analogues.

Authors:  M Isabel Calaza; Carlos Cativiela
Journal:  European J Org Chem       Date:  2008
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  5 in total

1.  Site-Selective Nitrene Transfer to Conjugated Olefins Directed by Oxazoline Peptide Ligands.

Authors:  Golo Storch; Naudin van den Heuvel; Scott J Miller
Journal:  Adv Synth Catal       Date:  2020-01-23       Impact factor: 5.837

2.  Stereospecific ring expansion of chiral vinyl aziridines.

Authors:  Matthew Brichacek; Mauricio Navarro Villalobos; Alexandra Plichta; Jon T Njardarson
Journal:  Org Lett       Date:  2011-02-10       Impact factor: 6.005

3.  Synthesis of novel 5-alkyl/aryl/heteroaryl substituted diethyl 3,4-dihydro-2H-pyrrole-4,4-dicarboxylates by aziridine ring expansion of 2-[(aziridin-1-yl)-1-alkyl/aryl/heteroaryl-methylene]malonic acid diethyl esters.

Authors:  Satish S More; T Krishna Mohan; Y Sateesh Kumar; U K Syam Kumar; Navin B Patel
Journal:  Beilstein J Org Chem       Date:  2011-06-20       Impact factor: 2.883

4.  Preparation and ring-opening reactions of N-diphenylphosphinyl vinyl aziridines.

Authors:  Ashley N Jarvis; Andrew B McLaren; Helen M I Osborn; Joseph Sweeney
Journal:  Beilstein J Org Chem       Date:  2013-05-02       Impact factor: 2.883

5.  Ring expansion of vinylaziridines through the strain-release pericyclic reaction: recent developments and applications.

Authors:  Yu Mi Heo; Seung-Mann Paek
Journal:  Molecules       Date:  2013-08-12       Impact factor: 4.411
  5 in total

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