Gold-Catalyzed Sequential Cyclization of 1-En-3,9-Diyne Esters to Partially Hydrogenated 3H-Dicyclopenta[a,b]naphthalenes

Weidong Rao, Joshua William Boyle, Philip Wai Hong Chan

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21 Citations (Scopus)

Abstract

A synthetic method that relies on a gold(I)-catalyzed cycloisomerization of 1-en-3,9-diyne esters to spiro[4.4]non-2-ene-substituted 1,2-dihydronaphthalenes is described. Robust with a wide variety of substitution patterns tolerated, the reaction provides the first example of a one-step strategy to construct such novel and architecturally challenging members of the carbocycle family in good to excellent yields. A mechanism is proposed in which the sequential cycloisomerization pathway was thought to involve a gold-catalyzed 1,3-acyloxy migration/Nazarov cyclization followed by a formal [4+2] cycloaddition to give the tetracarbocyclic product. A NHC-gold(I)-catalyzed sequential cycloisomerization of 1-en-3,9-diyne esters to partially hydrogenated 3H-dicyclopenta[a,b]naphthalenes, which are novel and architecturally challenging members of the carbocycle family of compounds, is described (see scheme; NHC=N-heterocyclic carbene).

Original languageEnglish
Pages (from-to)6532-6536
Number of pages5
JournalChemistry - A European Journal
Volume22
Issue number19
DOIs
Publication statusPublished - 4 May 2016

Keywords

  • carbocycles
  • cycloisomerization
  • gold
  • homogeneous catalysis
  • synthetic methods

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