Studies on the Reactivity of Cis-3-benzyloxy-1,2-epoxycyclohexane

Abstract

The reaction course of the selenation-oxidation-elimination sequence carried out from cis-4-benzyloxy-1,2-epoxycyclohexane (cis-1) is studied. Contrary to literature precedents, this transformation leads to an unexpected diastereomeric cyclohexenol, whose formation can be interpreted by stereoelectronic grounds. In addition, the base induced rearrangement of cis-1 with lithium amide bases is also discussed. In the absence of external additives, a mixture of cyclohexenols arising from the competition of syn and anti elimination processes is observed. However, in the presence of Li salts, the corresponding cyclohexenol arising from an apparent anti elimination pathway predominates. A mechanistic rationale is proposed to account for these observations.