SCHEDULED MAINTENANCE
Reaction of the anion of the (R*,S*) and (R*,S*) isomers of dimethyl (E-5-acetoxyhex-3-en-2-yl)malonate [(R*,R*)-(1) and (R*,S*)-(1)] in refluxing dimethoxyethane results in an intramolecular SN′ reaction, where the displacement of the acetate by the carbanion proceeds with syn stereochemistry (94–96%syn).
J. E. Bäckvall, J. O. Vågberg and J. P. Genêt, J. Chem. Soc., Chem. Commun., 1987, 159 DOI: 10.1039/C39870000159
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