Synthesis of a Troger's base analogue via stereoselective reductive coupling of N-phenylpiperazine to norbornane-2,5-dione

Abstract

The reaction of N-phenylpiperazines with norbornane-2,5-dione and NaCNBH3 gives the endo–endo dipiperazinyl norbornanes, which define a right triangular cavity potentially useful in host-guest chemistry as determined by X-ray crystallography and dipole moment measurements.