Keto furanylidene building blocks from silyl ethers of monoalkynylated β-keto carbonyls with iron(III) chloride hexahydrate-iodine

  • Brittany Garner
  • , Kristina Deveaux
  • , Laura Gessner
  • , Julia Trossarello
  • , Shuting Dai
  • , James W. Morgan
  • , Karelle Aiken

Research output: Contribution to journalArticlepeer-review

4 Scopus citations

Abstract

Keto furanylidene building blocks are synthesized from the unique silyl ethers of monoalkynylated β - keto carbonyls. The procedure consists of a desilylation, cyclization, and alkyne hydration facilitated by either a one-pot reaction with iron(III) chloride hexahydrateiodine or a two-step procedure with tosylic acid and gold(I) chloride. Notably, the hydration of the terminal alkyne with iron(III) chloride hexahydrate-iodine reagent is a safer and new alternative to the use of mercury(II) salts.

Original languageEnglish
Pages (from-to)181-187
Number of pages7
JournalHeterocyclic Communications
Volume18
Issue number4
DOIs
StatePublished - Oct 2012

Scopus Subject Areas

  • Organic Chemistry

Keywords

  • ( E)- diastereoselectivity
  • Deiodination
  • Furanylidene
  • Iodohydration

Fingerprint

Dive into the research topics of 'Keto furanylidene building blocks from silyl ethers of monoalkynylated β-keto carbonyls with iron(III) chloride hexahydrate-iodine'. Together they form a unique fingerprint.

Cite this