A Desymmetrization Route to Fused Tröger's Base Analogues: Synthesis, Isolation, and Characterization of the First Anti-Anti Diastereomer of a Fused Tris-Tröger's Base Analogue

A desymmetrization route to fused Troger's base analogues was developed. In this way, the synthesis of the first example of an anti-anti diastereomer of a fused tris-Troger's base analogue was accomplished. The resulting compound 5b is a nonlinear symmetric regioisomer obtained from p-bromoaniline in 7% yield. The corresponding syn-anti diastereomer 5a was obtained in 4% yield.