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RESEARCH PRODUCT

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

Lucia Anna BivonaMichelangelo GruttadauriaRenato NotoSerena RielaPaolo Lo Meo

subject

Homogeneous catalysiAqueous solutionSynthetic methodOrganic Chemistrychemistry.chemical_elementHomogeneous catalysisSettore CHIM/06 - Chimica Organicachemistry.chemical_compoundOrganocatalysiAldol reactionschemistrySuzuki reactionAldol reactionOrganocatalysisIonic liquidOrganic chemistryKnoevenagel condensationPhysical and Theoretical ChemistryPalladiumPalladium

description

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 %.

yearjournalcountryeditionlanguage
2012-03-13
10.1002/ejoc.201200092http://hdl.handle.net/10447/62813