Synthesis of cyclopentenones from cyclopropanes and silyl ynol ethers

Xiangbing Qi, Joseph M. Ready

Research output: Contribution to journalArticle

45 Citations (Scopus)

Abstract

(Chemical Equation Presented) Exploiting an opening: Lewis acid promoted ring-opening of donor-acceptor cyclopropanes generates a 1,3-zwitterion; cycloaddition with a silyl ynol ether leads to a general synthesis of cyclopentenones (see scheme). Substitution is tolerated on the ynol and on all positions of the cyclopropane to give tri-, tetra-, and penta-substituted cyclopentenones in high yield.

Original languageEnglish (US)
Pages (from-to)7068-7070
Number of pages3
JournalAngewandte Chemie - International Edition
Volume47
Issue number37
DOIs
StatePublished - Sep 1 2008

Fingerprint

Cyclopropanes
Ethers
Cycloaddition
Substitution reactions
Lewis Acids
Acids
Ether
cyclopentenone

Keywords

  • Cycloaddition
  • Cyclopentenones
  • Xyclopropanes
  • Ynols

ASJC Scopus subject areas

  • Chemistry(all)
  • Catalysis

Cite this

Synthesis of cyclopentenones from cyclopropanes and silyl ynol ethers. / Qi, Xiangbing; Ready, Joseph M.

In: Angewandte Chemie - International Edition, Vol. 47, No. 37, 01.09.2008, p. 7068-7070.

Research output: Contribution to journalArticle

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