Abstract

Geometrically and optically pure (3R,5E)- and (3R,5Z)-1,5-heptadien-3-ols undergo anionic oxy-Cope rearrangement under the exclusice control of oxyanion orientation with a 58-64% preference for equatorial oxygen. Six semicyclic dienols have also been synthesized where the preferred oxyanion-driven sigmatropic rearrangement pathway is obligatorily pitted against π-facial biases offered by 4-tert-butylcyclohexenyl, norbornenyl, and camphenyl rings. These rearrangements therefore offer especially stringent tests of those factors that control the level and direction of chirality transfer. The data show the oxyanion to disfavor becoming involved in 1,3-diaxial relationships

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