Diastereoselective α-allylation of secondary amines

We describe the diastereoselective α-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.

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