Optically active methyl (R)-3-oxo-7-(methoxycarbonyloxy)-8-nonenoate (1) underwent intramolecular allylation catalyzed by Pd(OAc)2-dppe in THF at room temperature to give racemic 3-vinyl-2-methoxycarbonylcyclohexanone (3), whereas similar palladium-catalyzed cyclization of a sodium salt of 1 proceeded very rapidly at 0 °C to form optically active 3, indicative of complete retention of the original chiral center.
No takes yet. Share an insight, caveat, or question.
Yamamoto et al. (1984) studied this question.
Synapse has enriched 5 related papers. Consider them for comparative context: