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

A Fernández-Mateos, SE Madrazo…

Index: Fernandez-Mateos; Encinas Madrazo; Herrero Teijon; Rubio Gonzalez Journal of Organic Chemistry, 2009 , vol. 74, # 10 p. 3913 - 3918

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Citation Number: 21

Abstract

Radical couplings of epoxides and nitriles mediated by Cp2TiCl provide a diastereoselective route to the synthesis of β-hydroxyketones. The conditions of this “aldol- like” reaction are mild enough to avoid the dehydration of the β-hydroxyketone. The scope of the coupling reaction with functionalized and tetrasubstituted epoxides has been studied. The radical character of the coupling reactions is demonstrated.