AlCl₃-catalyzed regioselective intermolecular α or γ mono- or α,γ bis-hydroalkoxylation of allenamides with alcohols

Regioselective intermolecular mono- or bis-hydroalkoxylation of allenamides with alcohols using simple aluminum-catalyzed reaction conditions is reported. When the reaction was carried out with 1.1 equivalents of alcohol at 50 °C, N,O-acetals were generated by 1,2-addition of an alcohol. An increase in temperature to 80 °C leads to γ-substituted ethers by an intermolecular isomerization process. Treatment with an excess of alcohol (3 equiv.) at 50 °C gave 1,3-bis(alkoxy)propanamines. The reactions exhibited good functional group tolerance and efficiency, affording the products in moderate to good yields.