(S)-cis-4-(1-Ethoxyethoxy)pent-2-en-1-ol reacts with methylmagnesium iodide in the presence of CuI to give (S)-2-methylpent-3-en-1-ol in an overall trans substitution, whereas (S)-trans-4-(1-ethoxyethoxy)pent-2-en-1-ol gives rise to the (R)-enantiomer, also in a trans substitution.
A. Claesson and L. Olsson, J. Chem. Soc., Chem. Commun., 1978, 621 DOI: 10.1039/C39780000621
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