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MICHELANGELO GRUTTADAURIA

Sequential Suzuki/Asymmetric Aldol and Suzuki/Knoevenagel Reactions Under Aqueous Conditions

  • Autori: Gruttadauria, M.; Bivona, L.; LO MEO, P.; Riela, S.; Noto, R.
  • Anno di pubblicazione: 2012
  • Tipologia: Articolo in rivista (Articolo in rivista)
  • Parole Chiave: Synthetic methods; Homogeneous catalysis; Organocatalysis; Palladium; Aldol reactions
  • OA Link: http://hdl.handle.net/10447/62813

Abstract

Here we describe for the first time a sequential Suzuki/asymmetric aldol reaction. Such sequential approach was achieved through the combined use of an ionic liquid supported palladium catalyst and the organocatalyst trans-4-(2,2-diphenylacetoxy)proline. Suzuki and asymmetric aldol reactions were performed under aqueous conditions. The use of a palladium catalyst under basic conditions allowed also the first example of sequential Suzuki/Knoevenagel reaction. Reactions were carried out under aqueous conditions and products were isolated in good to high yields and, in the case of the Suzuki/aldol reaction, with diastereoselectivities up to 91:9 and enantioselectivities up to at least 99%.