Rhenium-catalyzed synthesis of stereodefined cyclopentenes from β-ketoesters and aliphatic allenes

Salprima Yudha S, Yoichiro Kuninobu, Kazuhiko Takai

Research output: Contribution to journalArticle

19 Citations (Scopus)

Abstract

(Chemical Equation Presented) Come on allene: Commercially available [Re2(CO)10] as a catalyst provides five-membered carbocycles in moderate to excellent yields with high stereoselectivity (see scheme). The configuration at each of the three sp3 carbon centers of the ring is defined. The reaction proceeds at the β, γ, and adjacent methylene positions of the allene; previously, similar reactions usually occurred at the α, β, and γ positions of the allene.

Original languageEnglish
Pages (from-to)9318-9321
Number of pages4
JournalAngewandte Chemie - International Edition
Volume47
Issue number48
DOIs
Publication statusPublished - Nov 17 2008

Fingerprint

Rhenium
Cyclopentanes
Stereoselectivity
Catalysts
Carbon
Carbon Monoxide
propadiene

Keywords

  • Allenes
  • Cyclopentenes
  • Rhenium
  • Synthetic methods

ASJC Scopus subject areas

  • Chemistry(all)
  • Catalysis

Cite this

Rhenium-catalyzed synthesis of stereodefined cyclopentenes from β-ketoesters and aliphatic allenes. / Yudha S, Salprima; Kuninobu, Yoichiro; Takai, Kazuhiko.

In: Angewandte Chemie - International Edition, Vol. 47, No. 48, 17.11.2008, p. 9318-9321.

Research output: Contribution to journalArticle

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