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.
I. Fleming, K. Takaki and A. P. Thomas, J. Chem. Soc., Perkin Trans. 1, 1987, 2269 DOI: 10.1039/P19870002269
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