Treatment of γ-butyrolactone with bis[methoxy(thiocarbonyl)] disulfide in the presence of 2.2 equivalents of lithium diisopropylamide followed by the addition of aldehydes gave predominantly (E)-α-alkylidene-γ-butyrolactones. In contrast, when the reaction was carried out in the presence of metal salt such as cuprous iodide or zinc chloride, (Z)-α-alkylidene-γ-butyrolactone was obtained as the major product.
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Tanaka et al. (1980) studied this question.
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