Morpholino-azahomotricyclanimines-morpholine derivatives with a bulky cage-type substituent

Reductive amination of bicyclic cyanoketone 3 with benzylamine 5a provided morpholino-azahomotricyclanimine 6a. The crystal structure of cage compound 6a is reported. The dynamics of morpholine in 6a, in the debenzylated prod uct 6b/8 and in the amidinium salt 7a were investigated and compared with t hose in a bicyclic amidino analogue 14. The different and partial unexpecte d results were interpreted by studying the cyclopropane-morpholine rotation in 6b and 14 by molecular modeling and the C(2)-amino rotation in aminoace tamidine 15 by ab initio calculation. (C) 1999 Elsevier Science B.V. All ri ghts reserved.