Silylformylation-desilylation of propargyl amides: synthesis of alpha,beta-unsaturated aldehydes

LA Aronica, Patrizio Raffa, G Valentini, AM Caporusso*, P Salvadori

*Corresponding author for this work

Research output: Contribution to journalArticleAcademicpeer-review

8 Citations (Scopus)

Abstract

alpha, beta-Unsaturated aldehydes are prepared from easily available propargyl amides through a two-step sequence of silylformylation-desilylation reactions. The substituent on the nitrogen atom markedly influences both reactions, beta-silyalkenals being formed in the presence of tosyl or tert-butoxycarbonyl protected amines. TBAF is employed to induce the desilylation process that is performed under very mild experimental conditions. A contemporary elimination step occurs when tosylamido aldehydes are reacted affording 2-methylaryl-2-alkenals, while this process can be suppressed changing the functional group to NBOC, thus allowing the formation of beta-amino carbonyl compounds. (c) 2005 Elsevier Ltd. All rights reserved.

Original languageEnglish
Pages (from-to)527-530
Number of pages4
JournalTetrahedron Letters
Volume47
Issue number4
DOIs
Publication statusPublished - 23-Jan-2006
Externally publishedYes

Keywords

  • rhodium-catalysed silylformylation
  • desilylation
  • alpha,beta-unsaturated aldehydes
  • RHODIUM-CATALYZED TRANSFORMATION
  • ASYMMETRIC-SYNTHESIS
  • EFFICIENT SILYLFORMYLATION
  • ALDOL CONDENSATION
  • CARBONYL-COMPOUNDS
  • TERMINAL ALKYNES
  • 2-SILYLMETHYL-2-ALKENALS
  • 1-ALKYNES
  • COMPLEXES
  • ALKALOIDS

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