Lewis Base Catalyzed Ring Opening of Aziridines with Silylated Nucleophiles

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Abstract

The ring opening of N-tosylaziridines with trimethylsilylated nucleophiles, catalyzed by N,N,N‘,N‘-tetramethylethylenediamine, led to the production of β-functionalized sulfonamides in good to excellent yields with high regioselectivity.

Citing Articles

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This article has been cited by 14 ACS Journal articles (5 most recent appear below).

• 

  Synthetic Route to Chiral Tetrahydroquinoxalines via Ring-Opening of Activated Aziridines

  Manas K. Ghorai, Ashis K. Sahoo, and Sarvesh Kumar
  Organic Letters2011 13 (22), 5972-5975

  • Synthetic Route to Chiral Tetrahydroquinoxalines via Ring-Opening of Activated Aziridines

    Manas K. Ghorai, Ashis K. Sahoo, and Sarvesh Kumar
    Organic Letters2011 13 (22), 5972-5975

    A highly regio- and stereoselective route for the synthesis of racemic and nonracemic tetrahydroquinoxalines via the SN2-type ring-opening of activated aziridines with 2-bromoanilines followed by the Pd-catalyzed intramolecular C–N bond formation is ...

    Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links
• 

  Phosphine-Catalyzed Heine Reaction

  Allen Martin, Kathleen Casto, William Morris, and Jeremy B. Morgan
  Organic Letters2011 13 (20), 5444-5447

  • Phosphine-Catalyzed Heine Reaction

    Allen Martin, Kathleen Casto, William Morris, and Jeremy B. Morgan
    Organic Letters2011 13 (20), 5444-5447

    Aziridines are important synthetic intermediates which readily undergo ring-opening reactions. It is demonstrated that electron-rich phosphines are efficient catalysts for the regioselective rearrangement of N-acylaziridines to oxazolines. The reactions ...

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• 

  Diastereoselective Access to trans-2-Substituted Cyclopentylamines

  Antoine Joosten, Émilie Lambert, Jean-Luc Vasse, and Jan Szymoniak
  Organic Letters2010 12 (22), 5128-5131

  • Diastereoselective Access to trans-2-Substituted Cyclopentylamines

    Antoine Joosten, Émilie Lambert, Jean-Luc Vasse, and Jan Szymoniak
    Organic Letters2010 12 (22), 5128-5131

    A highly diastereoselective synthesis of trans-2-substituted cyclopentylamines via a tandem hydrozirconation/Lewis acid-mediated cyclization sequence applied to butenyl oxazolidines is described. The method allows an easy preparation of diversely ...

    Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links
• 

  Silver(I)−Diene Complexes as Versatile Catalysts for the C-Arylation of N-Tosylaziridines: Mechanistic Insight from In Situ Diagnostics

  Milan Bera and Sujit Roy
  The Journal of Organic Chemistry2010 75 (13), 4402-4412

  • Silver(I)−Diene Complexes as Versatile Catalysts for the C-Arylation of N-Tosylaziridines: Mechanistic Insight from In Situ Diagnostics

    Milan Bera and Sujit Roy
    The Journal of Organic Chemistry2010 75 (13), 4402-4412

    Silver(I) complex [Ag(diene)2]+Y− (where diene = cyclooctadiene, norbornadiene, and 1,3-cyclohexadiene; Y− = PF6−, BF4−) efficiently catalyzes the arylation of N-tosylaziridines with arenes and heteroarenes under ambient condition to provide the ...

    Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links
• 

  BF₃·OEt₂-Mediated Highly Regioselective S_N2-Type Ring-Opening of N-Activated Aziridines and N-Activated Azetidines by Tetraalkylammonium Halides

  Manas K. Ghorai, Amit Kumar and Deo Prakash Tiwari
  The Journal of Organic Chemistry2010 75 (1), 137-151

  • BF₃·OEt₂-Mediated Highly Regioselective S_N2-Type Ring-Opening of N-Activated Aziridines and N-Activated Azetidines by Tetraalkylammonium Halides

    Manas K. Ghorai, Amit Kumar and Deo Prakash Tiwari
    The Journal of Organic Chemistry2010 75 (1), 137-151

    A highly regioselective Lewis acid-mediated SN2-type ring-opening of N-sulfonylaziridines and azetidines with tetraalkylammonium halides in CH2Cl2 solution to afford 1,2- and 1,3-haloamines in excellent yields is described. An easy diastereoselective ...

    Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links

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