An efficient three-step synthesis of cyclopenta[b]pyrans via 2-donor-substituted fischer ethenylcarbenechromium complexes

Armin De Meijere, Heiko Schirmer, Frank Stein, Frank Funke, Michael Duetsch, Yao Ting Wu, Mathias Noltemeyer, Thomas Belgardt, Burkhard Knieriem

Research output: Contribution to journalArticlepeer-review

13 Citations (Scopus)

Abstract

A wide range of cyclopenta[b]pyrans 4 has been synthesized in a one-pot reaction by treatment of different 2-donorsubstituted ethenylcarbenechromium complexes 2 with alkynes in THF in moderate to excellent yields (41-90% for 14 out of 25 examples). The starting materials 2 are readily available in good to excellent yields (76-99% for 25 out of 36 examples) by Michael addition of amines, alcohols and thiols, respectively, to the corresponding alkynylcarbenechromium complexes 1. Due to their 10 π-electrons in a cross-conjugated bicyclic system, cyclopenta[b]pyrans have been termed pseudoazulenes, as they indeed have similar UV/Vis-spectroscopic properties.

Original languageEnglish
Pages (from-to)4132-4148
Number of pages17
JournalChemistry - A European Journal
Volume11
Issue number14
DOIs
Publication statusPublished - 2005 Jul 4

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Organic Chemistry

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