Remarkable Effect of Ethylene Gas in the Intramolecular Enyne Metathesis of Terminal Alkynes

Miwako Mori,* Norikazu Sakakibara, and Atsushi Kinoshita
Graduate School of Pharmaceutical Sciences, Hokkaido University, Sapporo 060-0812, Japan
J. Org. Chem., 1998, 63 (18), pp 6082–6083
DOI: 10.1021/jo980896e
Publication Date (Web): August 14, 1998
Copyright © 1998 American Chemical Society

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  • Cover Image

    Ethylene-Promoted versus Ethylene-Free Enyne Metathesis

    Anne G. D. Grotevendt, Justin A. M. Lummiss, Melanie L. Mastronardi, and Deryn E. Fogg
    Journal of the American Chemical Society2011 133 (40), 15918-15921
    • Ethylene-Promoted versus Ethylene-Free Enyne Metathesis

      Anne G. D. Grotevendt, Justin A. M. Lummiss, Melanie L. Mastronardi, and Deryn E. Fogg
      Journal of the American Chemical Society2011 133 (40), 15918-15921

      The role of ethylene in promoting metathesis of acetylenic enynes is probed within the context of ring-closing enyne metathesis, using first- and second-generation Grubbs catalysts. Under inert atmosphere, rapid catalyst deactivation is observed by ...

  • Cover Image

    From Highly Enantioselective Catalytic Reaction of 1,3-Diynes with Aldehydes to Facile Asymmetric Synthesis of Polycyclic Compounds

    Mark Turlington, Yuhao Du, Samuel G. Ostrum, Vishaka Santosh, Kathryne Wren, Tony Lin, Michal Sabat, and Lin Pu
    Journal of the American Chemical Society2011 133 (30), 11780-11794
    • From Highly Enantioselective Catalytic Reaction of 1,3-Diynes with Aldehydes to Facile Asymmetric Synthesis of Polycyclic Compounds

      Mark Turlington, Yuhao Du, Samuel G. Ostrum, Vishaka Santosh, Kathryne Wren, Tony Lin, Michal Sabat, and Lin Pu
      Journal of the American Chemical Society2011 133 (30), 11780-11794

      (S)-1,1′-Binaphth-2-ol (BINOL) in combination with ZnEt2, Ti(OiPr)4, and biscyclohexylamine was found to catalyze the highly enantioselective (83–95% ee) addition of various 1,3-diynes to aldehydes of diverse structures. This method provides a convenient ...

  • Cover Image

    Platinum(II) Chloride-Catalyzed Stereoselective Domino Enyne Isomerization/Diels−Alder Reaction

    Mathias Schelwies, Andreas Farwick, Frank Rominger, and Günter Helmchen
    The Journal of Organic Chemistry2010 75 (22), 7917-7919
    • Platinum(II) Chloride-Catalyzed Stereoselective Domino Enyne Isomerization/Diels−Alder Reaction

      Mathias Schelwies, Andreas Farwick, Frank Rominger, and Günter Helmchen
      The Journal of Organic Chemistry2010 75 (22), 7917-7919

      Chiral 1,6-enynes were prepared via Ir-catalyzed allylic substitutions. Their platinum(II) chloride-catalyzed domino enyne isomerization/Diels−Alder reaction provided stereoselective access to complex heterocycles. Very high diastereoselectivity was ...

  • Cover Image

    Asymmetric Allylic Alkylation in Combination with Ring-Closing Metathesis for the Preparation of Chiral N-Heterocycles

    Johannes F. Teichert, Suyan Zhang, Anthoni W. van Zijl, Jan Willem Slaa, Adriaan J. Minnaard, and Ben L. Feringa
    Organic Letters2010 12 (20), 4658-4660
    • Asymmetric Allylic Alkylation in Combination with Ring-Closing Metathesis for the Preparation of Chiral N-Heterocycles

      Johannes F. Teichert, Suyan Zhang, Anthoni W. van Zijl, Jan Willem Slaa, Adriaan J. Minnaard, and Ben L. Feringa
      Organic Letters2010 12 (20), 4658-4660

      Asymmetric copper-catalyzed allylic substitution with methylmagnesium bromide is employed in combination with ring-closing olefin metathesis or ene−yne metathesis to achieve the synthesis of chiral, unsaturated nitrogen heterocycles. The resulting six- ...

  • Cover Image

    Diastereoselective Synthesis of P-Stereogenic Heterocycles via Enyne Ring-Closing Metathesis

    James Stephen Harvey, Guy T. Giuffredi and Véronique Gouverneur
    Organic Letters2010 12 (6), 1236-1239
    • Diastereoselective Synthesis of P-Stereogenic Heterocycles via Enyne Ring-Closing Metathesis

      James Stephen Harvey, Guy T. Giuffredi and Véronique Gouverneur
      Organic Letters2010 12 (6), 1236-1239

      A range of P-containing ene-diynes suitable for desymmetrization was prepared via a two-step process starting from phosphorus oxychloride. In the presence of the Hoveyda−Grubbs II catalyst, these substrates underwent diastereoselective enyne ring-...

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History

  • Published In Issue September 04, 1998
  • Received May 13, 1998

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