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Several unsubstituted (E)-3-alkylmethylidene- and (E)-3-(arylmethylidene)-2(3H)-furanones have been synthesized in highly stereoselective fashion by mesylation-elimination of 3-(1-hydoxyalkyl)-2-silyloxyfurans. The latter were prepared from 2-triisopropylsilyloxy-3-bromofuran by halogen-lithium exchange and reaction of the in situ generated 3-lithiated silyloxyfuran with aldehydes.
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Boukouvalas et al. (2006) studied this question.
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