Rhodium complex-catalyzed Pauson-Khand-type reaction with aldehydes as a CO source

Takanori Shibata, Natsuko Toshida, Kentaro Takagi

Research output: Contribution to journalArticle

125 Citations (Scopus)

Abstract

With aldehydes as a CO source under solvent-free conditions, rhodium complex efficiently catalyzed an intramolecular carbonylative alkene-alkyne coupling (Pauson-Khand-type reaction) and various bicyclic enones were obtained in high yield. Experiments under argon flow and a 13C-labeling experiment suggested that almost no free carbon monoxide was generated in this reaction. When noncationic rhodium complex with chiral phosphine was used as a chiral catalyst, the reaction proceeded enantioselectively to give various chiral cyclopentenones in up to 90% ee under solvent-free conditions.

Original languageEnglish
Pages (from-to)7446-7450
Number of pages5
JournalJournal of Organic Chemistry
Volume67
Issue number21
DOIs
Publication statusPublished - 2002 Oct 18
Externally publishedYes

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Rhodium
phosphine
Carbon Monoxide
Aldehydes
Alkynes
Argon
Alkenes
Labeling
Experiments
Catalysts
cyclopentenone

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Rhodium complex-catalyzed Pauson-Khand-type reaction with aldehydes as a CO source. / Shibata, Takanori; Toshida, Natsuko; Takagi, Kentaro.

In: Journal of Organic Chemistry, Vol. 67, No. 21, 18.10.2002, p. 7446-7450.

Research output: Contribution to journalArticle

Shibata, Takanori ; Toshida, Natsuko ; Takagi, Kentaro. / Rhodium complex-catalyzed Pauson-Khand-type reaction with aldehydes as a CO source. In: Journal of Organic Chemistry. 2002 ; Vol. 67, No. 21. pp. 7446-7450.
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