Stereochemical outcome of benzyllithiums synthesis from selenides

Article abstract of DOI:10.1016/S0040-4039(00)92094-X

Epimerisation usually occurs during the synthesis of arylalcanes from the corresponding benzylselenides which involves benzyllithiums as intermediates. This has been used to produce stereoselectively arylcyclopentanes and arylcyclopropanes. γ-Benzenesulfonyloxyalkyl selenides substituted on the carbon bearing the benzenesulfonyl group behave differently and lead stereospecifically to arylcyclopropane derivatives.