Abstract:

One of the big challenges in organic chemistry is efficient enantioselective synthesis of acyclic compounds. The palladium-catalyzed coupling between arenediazonium salts and olefins (Heck-Matsuda reaction) represents a robust and accessible method for the synthesis of bioactive and structurally complex molecules. Our group is contributing significantly to the development of the stereo- and enantioselective Heck-Matsuda reaction. In 2013, we described a very practical and efficient method for the enantioselective arylation on acyclic allylic alcohols using commercial chiral bisoxazoline as ligand and several arenediazonium tetrafluoroborates as arylating agents in the presence of palladium trifluoroacetate Pd(TFA)2. To further demonstrate the scope and versatility of this method, we describe herein our preliminary results toward the intermolecular enantioselective Heck-Matsuda reaction of acyclic olefins diols with the main goal of synthesizing enantiomerically enriched aryl-θ-lactone as chiral building blocks, which are excellent precursors for the synthesis of bioactive molecules.