Diastereoselective α-allylation of secondary amines

We describe the diastereoselective alpha-allylation of various amines using an anodic oxidation-amidoalkylation sequence. Especially, we found that an acyclic amine, diethylamine, can be allylated with an excellent diastereoselectivity, as high as 94/6. Following our simple protocol, functionalized piperidine, pyrrolidine, morpholine, and tetrahydroisoquinoline were also obtained with moderate to good diastereomeric excesses and in good to excellent yields. (c) 2010 Elsevier Ltd. All rights reserved.