Tetrahedron letters

Samarium (II) iodide promoted reductive ring opening reaction of cyclopropane-1, 1-dicarboxylic esters. Synthesis of substituted 5-Pentanolides from carbonyl …

T Imamoto, T Hatajima, T Yoshizawa

Index: Imamoto, Tsuneo; Hatajima, Toshihiko; Yoshizawa, Takeshi Tetrahedron Letters, 1994 , vol. 35, # 42 p. 7805 - 7808

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Citation Number: 20

Abstract

Abstract Dimethyl cyclopropane-1, 1-dicarboxylate is readily subjected to reductive ring opening reaction with samarium (II) iodide in the presence of tris (dibenzoyl-methiodo) iron (III). The generated organosamarium intermediate is trapped by aliphatic ketones to afford 5, 5-disubstituted 2-methoxycarbonyl-5-pentanolides.