Zinc-Mediated Ring-Expansion and Chain-Extension Reactions of β-Keto Esters

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Abstract

The reaction of cyclic β-keto esters with CF₃CO₂ZnCH₂I provided the corresponding ring-expanded products in moderate to good yields. Although α-substituted acyclic β-keto esters reacted with much less efficient, chain-extension reaction of simple β-keto esters also proceeded effectively to generate γ-keto esters in high yields.

Citing Articles

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This article has been cited by 4 ACS Journal articles (4 most recent appear below).

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  A Mechanistic Investigation into the Zinc Carbenoid-Mediated Homologation Reaction by DFT Methods: Is a Classical Donor−Acceptor Cyclopropane Intermediate Involved?

  Wilhelm A. Eger, Charles K. Zercher, and Craig M. Williams
  The Journal of Organic Chemistry2010 75 (21), 7322-7331

  • A Mechanistic Investigation into the Zinc Carbenoid-Mediated Homologation Reaction by DFT Methods: Is a Classical Donor−Acceptor Cyclopropane Intermediate Involved?

    Wilhelm A. Eger, Charles K. Zercher, and Craig M. Williams
    The Journal of Organic Chemistry2010 75 (21), 7322-7331

    An extensive density functional theory (DFT, M05-2X) investigation has been performed on the zinc carbenoid-mediated homologation reaction of β-keto esters. The mechanistic existence of a classical donor−acceptor cyclopropane intermediate was probed to ...

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• 

  Preparation of a Storable Zinc Carbenoid Species and Its Application in Cyclopropanation, Chain Extension, and [2,3]-Sigmatropic Rearrangement Reactions

  Arnaud Voituriez, Lucie E. Zimmer and André B. Charette
  The Journal of Organic Chemistry2010 75 (4), 1244-1250

  • Preparation of a Storable Zinc Carbenoid Species and Its Application in Cyclopropanation, Chain Extension, and [2,3]-Sigmatropic Rearrangement Reactions

    Arnaud Voituriez, Lucie E. Zimmer and André B. Charette
    The Journal of Organic Chemistry2010 75 (4), 1244-1250

    The formation of a new phosphate carbenoid (n-BuO)2P(O)OZnCH2I and its application in organozinc-mediated reactions is described. This carbenoid undergoes very slow degradation in solution and can be stored for several weeks at −20 °C. Its reactivity was ...

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• 

  Zinc-Mediated C−C Bond Sigmatropic Rearrangement:  A New and Efficient Methodology for the Synthesis of β-Diketones

  Lezhen Li, Peijie Cai, Da Xu, Qingxiang Guo, and Song Xue
  The Journal of Organic Chemistry2007 72 (21), 8131-8134

  • Zinc-Mediated C−C Bond Sigmatropic Rearrangement:  A New and Efficient Methodology for the Synthesis of β-Diketones

    Lezhen Li, Peijie Cai, Da Xu, Qingxiang Guo, and Song Xue
    The Journal of Organic Chemistry2007 72 (21), 8131-8134

    A new and efficient methodology has been developed for the synthesis of β-diketones from aromatic α-bromo ketones in the presence of Furukawa reagent under mild conditions. The present transformation is proposed to proceed via a Reformatsky-type reaction ...

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• 

  Zinc-Mediated Chain Extension Reaction of 1,3-Diketones to 1,4-Diketones and Diastereoselective Synthesis of trans-1,2-Disubstituted Cyclopropanols

  Song Xue, Le-Zhen Li, Yong-Kang Liu, and Qing-Xiang Guo
  The Journal of Organic Chemistry2006 71 (1), 215-218

  • Zinc-Mediated Chain Extension Reaction of 1,3-Diketones to 1,4-Diketones and Diastereoselective Synthesis of trans-1,2-Disubstituted Cyclopropanols

    Song Xue, Le-Zhen Li, Yong-Kang Liu, and Qing-Xiang Guo
    The Journal of Organic Chemistry2006 71 (1), 215-218

    A variety of 1,3-diketones can be efficiently converted into the corresponding 1,4-diketones and trans-1,2-disubstituted cyclopropanols by using organozinc species in one-pot reactions. It was found that 2.3 equiv of CF3CO2ZnCH2I was effective to give the ...

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

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