Abstract The optically active (4S, 8S)-4, 8-bis (hydroxymethyl)-1, 5, 7-triazabicyclo [4.4. 0] dec-5-ene ((S, S)-1) has been synthesized in nine steps from L-asparagine with a total yield of 5.1%. Similarly, the enantiomer (R, R)-1 has been prepared from D-asparagine.(S, S)-and (S, S)-1 are representative examples of rigid and functionalized bicyclic guanidine systems and constitute useful intermediates in the construction of chiral selective anion-receptor ...