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: http://hdl.handle.net/10447/62813
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%.