Cross-coupling reactions between α,β-unsaturated ketones and aldehydes with CrCl2

Aldol condensation and cyclopropanol formation

Chika Toratsu, Takafumi Fujii, Takuma Suzuki, Kazuhiko Takai

Research output: Contribution to journalArticle

25 Citations (Scopus)

Abstract

In an aprotic solvent, dimethylformamide, a coupling reaction between an α,β-unsaturated ketone and an aldehyde is achieved with chromium(II) chloride. An intermolecular aldol reaction and an intramolecular cyclization proceed sequentially to give cis-2-hydroxyalkyl-substituted cyclopropanol stereoselectively [Eq. (a)].

Original languageEnglish
Pages (from-to)2725-2727
Number of pages3
JournalAngewandte Chemie - International Edition
Volume39
Issue number15
DOIs
Publication statusPublished - Aug 4 2000

Fingerprint

Dimethylformamide
Cyclization
Chromium
Ketones
Aldehydes
Chlorides
Condensation
cyclopropanol
3-hydroxybutanal

Keywords

  • Aldehydes
  • Aldol reactions
  • Chromium
  • Cross-coupling
  • Ketones

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Cross-coupling reactions between α,β-unsaturated ketones and aldehydes with CrCl2 : Aldol condensation and cyclopropanol formation. / Toratsu, Chika; Fujii, Takafumi; Suzuki, Takuma; Takai, Kazuhiko.

In: Angewandte Chemie - International Edition, Vol. 39, No. 15, 04.08.2000, p. 2725-2727.

Research output: Contribution to journalArticle

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AU - Takai, Kazuhiko

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AB - In an aprotic solvent, dimethylformamide, a coupling reaction between an α,β-unsaturated ketone and an aldehyde is achieved with chromium(II) chloride. An intermolecular aldol reaction and an intramolecular cyclization proceed sequentially to give cis-2-hydroxyalkyl-substituted cyclopropanol stereoselectively [Eq. (a)].

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