Assessing the utility of HAlCl2 derived vinylalanes for Michael addition

D. Willcox, H. Gondal, M.G. Civit, Simon Woodward

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Rare alkenylalanes are prepared by Cp2TiCl2 or Cp*2ZrCl2 (Cp = η-C5H5; Cp* = η-C5Me5) catalysed addition of HAlCl2·(THF)2 to terminal alkynes (R1CCH; R1 = alkyl). Use of minimum head-volume sealed vials maximises the hydroalumination yields of volatile alkynes. Facile 1,4-addition of the resultant alkenylalanes to unsaturated malonates R2CHC(CO2R3)2 (R2 = alkyl, aryl, R3 = alkyl) is observed providing rapid and convenient access to the addition products.
Original languageUndefined
Pages (from-to)1720-1721
Number of pages2
JournalTetrahedron Letters
Issue number10
Publication statusPublished - 2014


  • Hydroalumination
  • Conjugate addition
  • Alkenes
  • Michael reaction
  • Malonate

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