Gold-catalyzed dearomative spirocyclization of aryl alkynoate esters

Mark D. Aparece, Paul A. Vadola*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

69 Scopus citations

Abstract

Aryl alkynoate esters undergo gold-catalyzed spirocyclization under mild conditions, affording spirolactones in high yields. This approach obviates the need for stoichiometric halogenating reagents typically employed for alkyne activation in related transformations. Water was found to play a critical role in governing the product selectivity. Anhydrous conditions lead selectively to coumarin products, as has previously been observed for aryl alkynoate esters, while the addition of 1 equiv of water leads selectively to spirocycle formation.

Original languageEnglish (US)
Pages (from-to)6008-6011
Number of pages4
JournalOrganic Letters
Volume16
Issue number22
DOIs
StatePublished - Nov 21 2014

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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