RuHCl(CO)(PPh3)3-catalyzed reductive dimerization of α,β-unsaturated aldehydes leading to α-hydroxymethyl ketones

Takashi Doi, Takahide Fukuyama, Satoshi Minamino, Ilhyong Ryu*

*Corresponding author for this work

Research output: Contribution to journalArticle

28 Scopus citations

Abstract

The reductive dimerization α,β-unsaturated aldehydes to give saturated ketones was achieved using RuHCl(CO)(PPh3)3 as a catalyst in the presence of secondary alcohols as hydrogen source. The reaction is likely to proceed via the hydroruthenation of α,β-unsaturated aldehydes followed by aldol reaction of the resultant ruthenium enolates with α,β-unsaturated aldehydes to give unsaturated α-hydroxymethyl ketones, which undergo transfer hydrogenation to give α-hydroxymethyl ketones.

Original languageEnglish
Pages (from-to)3013-3016
Number of pages4
JournalSynlett
Issue number18
DOIs
StatePublished - 3 Nov 2006

Keywords

  • α,β-unsaturated aldehydes
  • α-hydroxymethyl ketones
  • Aldol reaction
  • Ruthenium enolates
  • Transfer hydrogenation

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