Catalyzed Olefin Isomerization Leading to Highly Stereoselective Claisen Rearrangements of Aliphatic Allyl Vinyl Ethers

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Abstract

Iridium(I)-catalyzed olefin isomerization in bis(allyl) ethers is integrated into a generally applicable strategy for affecting highly stereoselective Claisen rearrangements. Catalyzed alkene isomerization affords allyl vinyl ethers from easily prepared di(allyl) ethers; direct thermolysis of these reaction mixtures leads to highly diastereoselective [3,3] sigmatropic rearrangements affording syn-2,3-dialkyl-4-pentenal derivatives. An easily executed strategy for realizing asymmetric variants of the isomerization-Claisen rearrangement (ICR) reactions is also described.

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This article has been cited by 20 ACS Journal articles (5 most recent appear below).

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  Domino Alkene-Isomerization–Claisen Rearrangement Strategy to Substituted Allylsilanes

  Mark G. McLaughlin and Matthew J. Cook
  The Journal of Organic Chemistry2012 Article ASAP

  • Domino Alkene-Isomerization–Claisen Rearrangement Strategy to Substituted Allylsilanes

    Mark G. McLaughlin and Matthew J. Cook
    The Journal of Organic Chemistry2012 Article ASAP

    A one-pot isomerization–Claisen protocol has been developed for the synthesis of highly substituted allylsilanes. Monosilylated divinyl ethers can be isomerized using a cationic iridium(I) catalyst followed by a thermal Claisen rearrangement to provide ...

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

  Regioselective Synthesis of 2,3,4- or 2,3,5-Trisubstituted Pyrroles via [3,3] or [1,3] Rearrangements of O-Vinyl Oximes

  Heng-Yen Wang, Daniel S. Mueller, Rachna M. Sachwani, Rachel Kapadia, Hannah N. Londino, and Laura L. Anderson
  The Journal of Organic Chemistry2011 76 (9), 3203-3221

  • Regioselective Synthesis of 2,3,4- or 2,3,5-Trisubstituted Pyrroles via [3,3] or [1,3] Rearrangements of O-Vinyl Oximes

    Heng-Yen Wang, Daniel S. Mueller, Rachna M. Sachwani, Rachel Kapadia, Hannah N. Londino, and Laura L. Anderson
    The Journal of Organic Chemistry2011 76 (9), 3203-3221

    The regioselective synthesis of 2,3,4- or 2,3,5-trisubstituted pyrroles has been achieved via [3,3] and [1,3] sigmatropic rearrangements of O-vinyl oximes, respectively. Iridium-catalyzed isomerization of easily prepared O-allyl oximes enables rapid ...

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

  Carbon−Carbon Bond Formation and Pyrrole Synthesis via the [3,3] Sigmatropic Rearrangement of O-Vinyl Oxime Ethers

  Heng-Yen Wang, Daniel S. Mueller, Rachna M. Sachwani, Hannah N. Londino and Laura L. Anderson
  Organic Letters2010 12 (10), 2290-2293

  • Carbon−Carbon Bond Formation and Pyrrole Synthesis via the [3,3] Sigmatropic Rearrangement of O-Vinyl Oxime Ethers

    Heng-Yen Wang, Daniel S. Mueller, Rachna M. Sachwani, Hannah N. Londino and Laura L. Anderson
    Organic Letters2010 12 (10), 2290-2293

    A new method for the synthesis of 2,4- and 2,3,4-substituted pyrroles in two or three steps from commercially available ketones and allyl hydroxylamine is described. An iridium-catalyzed isomerization reaction has been developed to convert O-allyl ...

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

  Copper-Promoted Coupling of Vinyl Boronates and Alcohols: A Mild Synthesis of Allyl Vinyl Ethers

  Ryan E. Shade, Alan M. Hyde, John-Carl Olsen and Craig A. Merlic
  Journal of the American Chemical Society2010 132 (4), 1202-1203

  • Copper-Promoted Coupling of Vinyl Boronates and Alcohols: A Mild Synthesis of Allyl Vinyl Ethers

    Ryan E. Shade, Alan M. Hyde, John-Carl Olsen and Craig A. Merlic
    Journal of the American Chemical Society2010 132 (4), 1202-1203

    A copper-promoted coupling of vinyl pinacol boronate esters and alcohols for the synthesis of enol ethers is reported. The reaction occurs in 50−99% yield and is compatible with a variety of functional groups. Cupric acetate is the copper source, and ...

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

  Cationic Rhodium(I)−dppf Complex-Catalyzed Olefin Isomerization/Propargyl Claisen Rearrangement/Carbonyl Migration Cascade

  Ken Tanaka, Eri Okazaki and Yu Shibata
  Journal of the American Chemical Society2009 131 (31), 10822-10823

  • Cationic Rhodium(I)−dppf Complex-Catalyzed Olefin Isomerization/Propargyl Claisen Rearrangement/Carbonyl Migration Cascade

    Ken Tanaka, Eri Okazaki and Yu Shibata
    Journal of the American Chemical Society2009 131 (31), 10822-10823

    We have established that a cationic rhodium(I)−dppf complex catalyzes isomerizations of allyl propargyl ethers to allenic aldehydes in good yields from room temperature to 40 °C. On the other hand, carbonyl migration reactions from allenic aldehydes ...

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

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