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Pent-3-yn-2-yl acetate (1) reacts with dimethyl(phenyl)silyl cuprate reagent to give a mixture of allenylsilane and propargylsilane. The corresponding N-phenylcarbamate (4) gives only the allenylsilane. Four other examples of this regioselective reaction are reported. The stereochemistry is largely syn.
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Fleming et al. (1987) studied this question.
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