Stereochemistry of the organocuprate reactions of two cis–trans isomeric allylic ethers
- 1 January 1978
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Chemical Communications
- No. 14,p. 621-623
- https://doi.org/10.1039/c39780000621
Abstract
(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.Keywords
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