The electrochemical cyanation of N-benzyl-substituted cyclic TMS counterparts. Both the stereoselectivity and regioselectivity of the cyanide addition were investigated six-membered α-silylamines including tetrahydroquinoline and piperidine derivatives was studied. The results of these with 3-methylpiperidine as the model compound. The formation of a single cis diastereoisomer in which the 2-investigations demonstrate that α-silylamines are valuable precursors for the preparation of the corresponding αcyano group is axial and the 5-methyl group is equatorial, indicates that the addition of the cyanide anion onto the cyanoamines. The TMS group α to the N atom not only governs the chemoselectivity of the iminium formation iminium species is under stereoelectronic control. In addition, the redox reaction involving the intermediate through a preferential desilylation reaction under the experimental conditions (i.e., amine cation radical nitrogen-centered cation radical and the cyanide anions played no role, because the α-silyl radical has such a short desilylation versus deprotonation), it also lowers the oxidation potential of tertiary amines compared to their non-lifetime.
lectivity with the electrochemical method limits its utility [a] Laboratoire dЈElectrochimie et dЈOrganome ´talliques, came clear that the regioselectivity of the cyanide addition