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(E)-1-Methoxymethoxybut-2-enyl(tributyl)stannane (6), readily available by the addition of tributylstannyl-lithium to crotonaldehyde and alkylation of the adduct using chloromethyl methyl ether, reacts on heating with aldehydes to give anti-4-hydroxy-3-methyl-cis-1,2-enol ethers. These on hydrolysis and oxidation provide trans-4,5-disubstituted butyrolactones.
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Pratt et al. (1989) studied this question.
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