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Keywords:

  • 1,6-addition;
  • allenes;
  • conjugated enynes;
  • Grignard reagents;
  • iron

Abstract

Treatment of 2-alken-4-ynoates with methyl- or aryl-Grignard reagents and iron(II) chloride (10 mol%) afforded 5-methyl- or 5-aryl-3,4-alkadienoates in good yields as a single isomer after aqueous work-up. Likewise, (2-alken-4-ynoyl)oxazolidinones afforded (5-methyl-3,4-alkadienoyl)oxazolidinones. The aldol-type reaction with acetone was also possible in place of the hydrolytic work-up.