Two exceptionally long NaO distances in Li/Na enolate 1 lead to a unique “open-stack” structure (sketch of the framework depicted on the right). This can be used as a model for the intermediates in aldol reactions. The two outer sodium atoms in the stack are bound to amine ligands, which can thus influence the selectivity of an attack on the enolate.
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Henderson et al. (1995) studied this question.
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