Sequential Oxidative α‑Cyanation/Anti-Markovnikov
Hydroalkoxylation of Allylamines

Org. Lett. 2015, 17, 4770−4773

Org. Lett.

Iron-catalyzed oxidative α-cyanations at tertiary allylamines in the allylic position are followed by anti-Markovnikov additions of alcohols across the vinylic CC double bonds of the initially generated α-amino nitriles. These consecutive reactions generate 2-amino-4-alkoxybutanenitriles from three reactants (allylamines, trimethylsilyl cyanide, and alcohols) in one reaction vessel at ambient temperature.

TU München