Tetrahedron letters

Vicinal dianions of diethyl α-aroylsuccinates: a general synthetic route to α-aroyl-and α-arylidene-γ-butyrolactones

M Pohmakotr, L Sampaongoen, A Issaree, P Tuchinda…

Index: Pohmakotr, Manat; Sampaongoen, Laddawan; Issaree, Arisara; Tuchinda, Patoomratana; Reutrakul, Vichai Tetrahedron Letters, 2003 , vol. 44, # 35 p. 6717 - 6720

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Citation Number: 18

Abstract

Vicinal dianions derived from diethyl α-aroylsuccinates were found to react with carbonyl compounds β-regioselectively to afford α-aroyl-γ-butyrolactones, which were converted into α-arylidene-γ-butyrolactones by reduction with H2/Pd–C followed by elimination employing methanesulfonyl chloride in pyridine. The method provides a general and convenient route to α-aroyl-and α-arylidene-γ-butyrolactones.