REGIOSPECIFIC FUNCTIONALISATION OF CARBON ATOMS α TO HETEROCYCLIC NITROGEN

Article abstract of DOI:10.1016/S0040-4020(01)88573-2

Previously, methods have been devised to functionalise the two endocyclic C atoms α to the piperidine N.In the present study we show that a nitrile substituent can be introduced also to the exocyclic α-C, making the centre either nucleo- or electrophilic in subsequent transformations.NMR studies have been used to gain knowledge of the mechanistic aspects leading to the observed regiospecificity.The generality of the method, along with the ease of operation, high yields and regiospecificity, make it highly versatile for synthetic purposes.