Pseudoephedrine-Derived Myers Enolates: Structures and Influence of Lithium Chloride on Reactivity and Mechanism

The structures and reactivities of pseudoephedrine-derived dianionic Myers enolates are examined. A combination of NMR and IR spectroscopic, crystallographic, and computational data reveal that the homoaggregated dianions form octalithiated tetramers displaying S4-symmetric Li8O8 cores and overall C2 symmetry. Computational and isotopic labeling studies reveal strong N–Li contacts in the carboxamide enolate moiety. The method of continuous...