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Stereoselective Decarboxylative Alkylation of Titanium(IV) Enolates with Diacyl Peroxides

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journal contribution
posted on 11.12.2019, 16:50 by Alejandro Gómez-Palomino, Marina Pérez-Palau, Pedro Romea, Fèlix Urpí, Marc Del Olmo, Timo Hesse, Sonja Fleckenstein, Enrique Gómez-Bengoa, Lia Sotorríos, Mercè Font-Bardia
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.