Assignment of configuration of larger bicyclo[n.1.0]alkylamines. The use of a lanthanide shift reagent

Abstract

The detection of the endo- or exo-position for the amino-function in methylbicyclo[n.1.0]alkylmorpholines is accomplished by use of a lanthanide shift reagent. This method is particularly useful for larger[n.1.0]bicyclic systems because of the impossibility of establishing the configuration on the basis of the dynamics of the morpholino group. The differences in the chemical shifts caused by complexation of an endo- or an exo-amine are studied for the isomers of bicyclo[3.1.0]hexylmorpholine. A method for the preparation of sterically pure methylbicyclo[n.1.0]alkylmorpholines is described.