Improving Tröger's Base Chemistry : Developing the Chemistry of Tröger's base

Sammanfattning: The Tröger’s base framework has been implemented in two different receptors. The first of these receptors, incorporating two 18-crown-6 moities, was used as a host in a binding study together with a sieries of bisammonium salts that yielded different binding constants that were then used as a benchmark to compare different computational methods (Molecular Mechanics (MM) and Density Functional Theory (DFT)) in predicting the correct results where the MM methods proved more effective. The second of the receptors incorporated two Tröger’s base moieties linked together with two crown ether straps. This receptor was tested for it’s affinity towards different metal cations, the receptor proved too hindered to accomodate any cations except Fe3+. Furthermore, the reactivity of Tröger’s base with lithium amide bases has been investigated extensively. A new protocol for preparing mono- and bissubstistuted Tröger’s base derivatives has been developed where Tröger’s base is treated with sBuLi/TMEDA followed by an electrophilic quench resulting in a Tröger’s base derivative substituted in the exo-6 and exo-12 positions. In addition to this method, a method for converting exo-6- and exo-12 substituted Tröger’s base amides into endo-6 and endo-12 substituted Tröger’s base amide has been developed. A study of the reduction of Tröger’s base amides is described herein.