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MICHELANGELO GRUTTADAURIA

First evidence of proline as bifunctional catalyst in the Baylis-Hillman reaction between alkyl vinyl ketones and arylaldehydes

  • Autori: Gruttadauria, M.; Giacalone, F.; MOSSUTO MARCULESCU, A.; LO MEO, P.; Riela, S.; Noto, R.
  • Anno di pubblicazione: 2008
  • Tipologia: Articolo in rivista (Articolo in rivista)
  • OA Link: http://hdl.handle.net/10447/32023

Abstract

Proline in the presence of sodium hydrogen carbonate has been found to be an effective catalyst for the Baylis–Hillman reaction between methyl or ethyl vinyl ketone and aryl aldehydes. Screening of several amine catalysts showed that an ionizable carboxylic function directly linked to the secondary amine catalyst plays an important role in the synthesis of the desired product in good yield. The data obtained has allowed us to suggest, for the first time, that proline, sarcosine, pipecolinic acid and homoproline may act as bifunctional catalysts via a bicyclic enaminolactone species as intermediate. Quantum-mechanical calculations (PM3/COSMO and ab initio 3-21G/COSMO) support this mechanism and give more insight into the role of hydrogen carbonate.