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New Synthetic Developments

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Part of the Reactivity and Structure Concepts in Organic Chemistry book series (REACTIVITY,volume 26)

Abstract

Lee and Richardson have disclosed that it is entirely feasible to cyclopentannulate silyl enol ethers in a one-pot two-step process. For example, condensation of 1 with the readily available stannane 2 in the presence of trimethylsilyl triflate leads to an adduct that cyclizes to 3 on subsequent exposure to titanium tetrachloride [5]. This new strategy is notable in that a doubly functionalized product results. 1,2-Bis(trimethylsilyloxy)cyclopentene (4) condenses with chloride 5 in the presence of anhydrous zinc chloride to give a 1:1 mixture of 6 and 7 [6]. The first relevant point is that alkylation proceeds without annihilation of the allylsilane moiety. Consequently, this functionality is available for subsequent ring closure as illustrated by the independent conversion of 6 and 7 to 8 and 9, respectively, when treated with ethylaluminum dichloride.

Keywords

  • Ring Expansion
  • Diazo Ketone
  • Synthetic Development
  • Anhydrous Zinc Chloride
  • Silyl Enol Ether

These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

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  • DOI: 10.1007/978-3-642-72598-2_2
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© 1987 Springer-Verlag Berlin Heidelberg

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Paquette, L.A., Doherty, A.M. (1987). New Synthetic Developments. In: Polyquinane Chemistry. Reactivity and Structure Concepts in Organic Chemistry, vol 26. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-72598-2_2

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  • DOI: https://doi.org/10.1007/978-3-642-72598-2_2

  • Publisher Name: Springer, Berlin, Heidelberg

  • Print ISBN: 978-3-642-72600-2

  • Online ISBN: 978-3-642-72598-2

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