For a projected total synthesis of the morphine alkaloids, Jung et al. discovered an efficient synthesis of 2-ethenylcyclopropyl aryl ketones via an intramolecular S<sub>N</sub>2-like displacement of allylic esters. A novel 1,5-acyl shift process is observed that contributes to a mixture of products. Density functional theory studies provide insights into the mechanism of this rearrangement-cyclization process and provide a rationale for the observed product ratios.

Computational studies on the mechanism of base-promoted rearrangement-cyclization of allylic esters

253rd National Meeting (2017)

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