Tetrahedron letters

Titanocene (III) chloride mediated radical-induced one-pot synthesis of α-methylene-γ-butyrolactones

M Paira, B Banerjee, S Jana, SK Mandal, SC Roy

Index: Paira, Moumita; Banerjee, Biplab; Jana, Samaresh; Mandal, Samir Kumar; Roy, Subhas Chandra Tetrahedron Letters, 2007 , vol. 48, # 18 p. 3205 - 3207

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Citation Number: 15

Abstract

A simple and efficient methodology has been developed for the one-pot preparation of α- methylene-γ-butyrolactones by free-radical induced Barbier-type reaction of methyl 2- (bromomethyl) acrylate and aldehydes followed by in situ lactonization. The radical initiator titanocene (III) chloride (Cp2TiCl) was easily generated in situ from commercially available Cp2TiCl2 and activated zinc dust in THF. Ketones remained unaffected under the reaction ...