Unusual Nazarov cyclization in near-critical water

Tuomo Leikoski, Juha Kaunisto, Martti Alkio, Olli Aaltonen, Jari Yli-Kauhaluoma

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7 Citations (Scopus)

Abstract

The Nazarov reaction of trans,trans-dibenzylidene acetone in near-critical water with or without additional carbon dioxide produces 2,3-diphenyl-2-cyclopentenone instead of the conventional Nazarov product, 3,4-disubstituted 2-cyclopentenone. The use of organic solvents and strong mineral acids, generally required for this reaction, is avoided by using water and carbonic acid as a proton source. After an optimization procedure, 38% yield of 2,3-diphenyl-2-cyclopentenone was obtained. The presence of carbon dioxide had a clear positive effect on yield.
Original languageEnglish
Pages (from-to)629-633
JournalOrganic Process Research and Development
Volume9
Issue number5
DOIs
Publication statusPublished - 2005
MoE publication typeA1 Journal article-refereed

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Keywords

  • Nazarov reaction
  • cyclopentenones
  • cyclization
  • ketones

Cite this

Leikoski, T., Kaunisto, J., Alkio, M., Aaltonen, O., & Yli-Kauhaluoma, J. (2005). Unusual Nazarov cyclization in near-critical water. Organic Process Research and Development, 9(5), 629-633. https://doi.org/10.1021/op050075t