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Stereoselective Decarboxylative Alkylation of Titanium(IV) Enolates with Diacyl Peroxides
Alejandro Gómez-Palomino1, Marina Pérez-Palau1, Pedro Romea1
1Secció de Química Orgànica, Departament de Química Inorgànica i Orgànica and Institut de Biomedicina de la Universitat de Barcelona (IBUB) , Universitat de Barcelona , Carrer Martí i Franqués 1-11 , 08028 Barcelona , Catalonia , Spain.
Abstract:
Simple treatment of chiral titanium(IV) enolates with diacyl peroxides produces highly diastereoselective decarboxylative alkylations to efficiently deliver the corresponding adducts, most of which are not accessible through any of the current alkylating procedures. Such an unprecedented alkylation proceeds through an SET process that triggers the decomposition of the peroxide into a carbon-centered radical that finally combines with the resulting Cα radical. The procedure has been applied to the enantioselective synthesis of arundic acid.
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