We report efficient stereoselective and high yielding syntheses of each of the four enantiomers of phenylcyclopentanes bearing a quaternary center and a E-propenyl chain on the adjacent carbon that involves intramolecular allylic substitution reactions. In complement to its synthetic value, this process models the SN' reaction and allows prediction of its stereochemical outcome.
- Aryl cyclopentanes
- Benzyl selenides
- Se/Li exchange
- SN' reaction
- Stereospecific carbocyclization