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

ABSTRACT: 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 variations proves deceptive, as octalithiated tetrameric homoaggregates afford hexalithiated trimeric heteroaggregates. A lithium diisopropylamide-lithium enolate mixed aggregate is found to be a C₂-symmetric hexalithiated species incorporating two enolate dianions and two lithium diisopropylamide (L

SUBMITTER: Zhou Y 

PROVIDER: S-EPMC7079698 | biostudies-literature | 2019 Apr

REPOSITORIES: biostudies-literature