Journal of Organometallic Chemistry

Synthesis of γ-lactones and unsaturated bis γ-lactones via Cu–Fe-mediated reductive cyclization of di-and tri-α-halogenated carboxylic esters

I Somech, Y Shvo

Index: Somech, Iris; Shvo, Youval Journal of Organometallic Chemistry, 2000 , vol. 601, # 1 p. 153 - 159

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Citation Number: 8

Abstract

A new synthetic route to γ-substituted γ-butyrolactones from alkenes and α-dichloro ester, in the presence of CuCl (catalytic) and Fe (0)(stoichiometric) in acetonitrile, was established. A study of this reaction has demonstrated that the overall process consists of the following reaction steps:(a) addition of the dichloro ester to the olefin via CuCl catalysis;(b) selective reduction of the α-chloro atom in the resulting adduct by Fe (0);(c) cyclization of the ...