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MICHELANGELO GRUTTADAURIA

Advances towards highly active and stereoselective simple and cheap proline-based organocatalysts

  • Autori: Giacalone, F.; Gruttadauria, M.; Agrigento, P.; LO MEO, P.; Noto, R.
  • Anno di pubblicazione: 2010
  • Tipologia: Articolo in rivista (Articolo in rivista)
  • Parole Chiave: Aldol reactions; Asymmetric catalysis; Organocatalysis; Water chemistry
  • OA Link: http://hdl.handle.net/10447/51116

Abstract

Ten 4-acyloxy-L-prolines were screened as catalysts at loadings of 2–0.1 mol-% for the direct asymmetric aldol reaction in water by using variable amounts of water. Among them, a new catalyst, the L-proline carrying a trans-4-(2,2-diphenylacetoxy)group, and a catalyst previously synthesized by us, the L-proline carrying a trans-(4-phenylbutanoyloxy)group, were found to be excellent catalysts for the aldol reaction between cyclohexanone or cyclopentanone and substituted benzaldehydes when employed in only 1 and 0.5 mol-%,respectively, at room temperature without additives. For such catalysts, high turnover numbers were obtained, which are among the highest values obtained for enamine organocatalysis. Finally, these catalysts can be synthesized by direct O-acylation from inexpensive molecules and successfully used in scaled-up reactions.