Synthesis of Versatile Nonsymmetric Amine- and Boron-Functionalized Tröger's Base Derivatives, Including a Tröger's Base Amino Acid

Abstract

Troger's base is a building block with a unique rigidity and geometry that has an increasing number of applications in a variety of nanoscale chemistry projects. This paper describes the facile synthesis of a set of Troger's base derivatives that have lost their C2 symmetry by virtue of having each ring differentiated, and contain amine, carboxylate, halogen, and/or boronate substituents to enable a large number of different cross-coupling and amide coupling reactions. We also describe the synthesis and preliminary chiral resolution of a new Troger's base amino acid building block.