Titanocene-Promoted Intermolecular Couplings of Epoxides with Nitriles. An Easy Access to β-Hydroxyketones

Abstract

Radical couplings of epoxides and nitriles mediated by Cp(2)TiCl provide a diastereoselective route to the synthesis of beta-hydroxyketones. The conditions of this "aldol-like" reaction are mild enough to avoid the dehydration of the beta-hydroxyketone. The scope of the coupling reaction with functionalized and tetrasubstituted epoxides has been studied. The radical character of the coupling reactions is demonstrated.