REDUCTIVE DECYANATION OF ANNULATED AMINOCYCLOPROPANE-ENDO-CARBONITRILES - A WAY TO ANNULATED CYCLOPROPANE-EXO-AMINES

Annulated Aminocyclopropane-endo-carbonitriles 11a,b are reductively d ecyanated by sodium in liquid ammonia with complete retention of confi guration. An additionally existing chlorine atom in the starting mater ials 12a,c-e, thereby, is simultaneously replaced by hydrogen. The pre parative advantage of this method is demonstrated by the selective acc ess to 6 alpha-H-isomers 13b and 13e as members of the ensemble of bic yclo[3.1.0]hexanediyl-dimorpholine diastereomers. A strong buckled bic yclohexane unit is present in 3 alpha,6 alpha-isomer 13e as indicated by H-1 NMR spectroscopy and X-ray structural analysis.