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

  • Authors: Gruttadauria, M; Bivona, LA; Lo Meo, P; Riela, S; Noto, R
  • Publication year: 2012
  • Type: Articolo in rivista (Articolo in rivista)
  • Key words: Synthetic methods; Homogeneous catalysis; Organocatalysis; Palladium; Aldol reactions
  • OA Link:


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%.