Abstract
Model compounds have been studied to elucidate the relative orientation of enolate and carbonyl moieties in the aldol reaction. The syntheses of these compounds have been achieved from a common precursor derived from fragmentation of adamantane. Models of the limiting transition structures reveal that the cyclization must proceed through either a synclinal or antiperiplanar orientation of the aldehyde with respect to the enolate. The origin of the selectivities and the implication for enolate and transition structures are discussed
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