FeCl3 center dot 6H(2)O-catalyzed Mukaiyama-aldol type reactions of enolizable aldehydes and acetals

Alejandra Rodríguez-Gimeno, Ana B. Cuenca, Jesús Gil-Tomás, Mercedes Medio-Simón, Andrea Olmos, Gregorio Asensio

Research output: Indexed journal article Articlepeer-review

18 Citations (Scopus)

Abstract

Mukaiyama-aldol type reactions of acetals derived from enolizable aldehydes with FeCl3 center dot 6H(2)O, an eco-friendly, low-cost, and stable catalyst, lead to beta-methoicycarbonyl compounds with nearly quantitative yields. The methodology is extended to the parent aldehydes as starting materials, leading to the corresponding aldols with lower yields, but efficiently. Different alkyl and aryl substituted acetals and aldehydes have been tested in the reaction with linear and cyclic silyl enol ethers. Reactions are carried out in an open air atmosphere, and additives are not required. Acetals can be considered activating groups of the carbonyl moiety rather than a protecting group in this type of FeCl3 center dot 6H(2)O-catalyzed condensation.
Original languageEnglish
Pages (from-to)8263-8270
Number of pages8
JournalJournal of Organic Chemistry
Volume79
Issue number17
DOIs
Publication statusPublished - 5 Sept 2014
Externally publishedYes

Keywords

  • Enol silyl ethers
  • Lewis-acid
  • Substitution-reactions
  • Organosilicon compounds
  • Catalyzed reactions
  • Mannich reactions
  • Aqueous-media
  • Iron
  • Induction
  • Carbonyl

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