The lack of stereoselectivity in the Stobbe condensation involving acetophenone or diethyl α-phenylethylidene-succinate can be attributed to E2 elimination through both diastereoisomeric lactone intermediates, base catalysed isomerisation of ester reactant or product(s), or a combination of these reactions.
H. G. Heller and M. Szewczyk, J. Chem. Soc., Perkin Trans. 1, 1974, 1483 DOI: 10.1039/P19740001483
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