Synthesis of tricyclic triamines using intramolecular cycloaddition of nitrones

Abstract

Tricyclic triamines were synthesized through intramolecular cycloaddition of nitrones with an eight-membered cyclic alkene unit. The cyclic alkene unit was readily prepared via ring-closing metathesis. The cycloaddition proceeded regioselectively, affording products containing a bicyclo[4.2.1] skeleton. The origin of the regioselectivity was further examined using density functional theory (DFT) calculations.