Abstract
The chiral diether ligand controlled asymmetric conjugate addition of organolithiums to nona-2,7-dienedioates preferentially proceeds via the <i>s</i>-<i>cis</i> conformation with coordination of the carbonyl oxygen atom to the lithium to give a lithium <i>E</i>-enolate intermediate. Subsequent intramolecular conjugate addition of the enolate also proceeds via a cyclic transition state involving the lithium and the <i>s</i>-<i>cis</i>-enoate, resulting in <i>trans</i>,<i>trans</i>-trisubstituted cyclohexanes with high enantiomeric excesses and yields.
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