Synthesis of multisubstituted cyclopentadienes from cyclopentenones prepared via catalytic double aldol condensation and nazarov reaction sequence

Yuta Nishina, Tomohiro Tatsuzaki, Ayano Tsubakihara, Yoichiro Kuninobu, Kazuhiko Takai

Research output: Contribution to journalArticle

5 Citations (Scopus)

Abstract

The rhenium-catalyzed synthesis of cyclopentenone derivatives via double aldol condensation and successive Nazarov reaction is described. The cyclopentenones were converted to the corresponding cyclopentadienes using organolithium reagents. Cyclopentadienes with four different substituents could be synthesized by stepwise double aldol condensation using a ketone and two types of aldehydes, followed by treatment with an organolithium reagent.

Original languageEnglish
Pages (from-to)2585-2589
Number of pages5
JournalSynlett
Issue number17
DOIs
Publication statusPublished - 2011

Fingerprint

Cyclopentanes
Condensation
Rhenium
Ketones
Aldehydes
Derivatives
3-hydroxybutanal
cyclopentenone

Keywords

  • aldol condensation
  • cyclopentadiene
  • cyclopentenone
  • Nazarov cyclization
  • rhenium

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Synthesis of multisubstituted cyclopentadienes from cyclopentenones prepared via catalytic double aldol condensation and nazarov reaction sequence. / Nishina, Yuta; Tatsuzaki, Tomohiro; Tsubakihara, Ayano; Kuninobu, Yoichiro; Takai, Kazuhiko.

In: Synlett, No. 17, 2011, p. 2585-2589.

Research output: Contribution to journalArticle

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