Direct and Stereoselective Iron-Catalyzed Amidation of Binor-S with Alkyl and Aryl Cyanides in Water

Abstract

The amidation of heptacyclo[8.4.0.02,12.03,8.04,6.05,9.011,13]tetra­decane (binor-S) with aceto-, propio-, valero-, and benzonitrile was performed in the presence of water and FeCl3·6H2O as catalyst to give the corresponding 10-exo-amidohexacyclo[9.2.1.02,7.03,5.04,8.09,13]tetradecanes. Hydrolysis of 10-exo-acetamidohexacyclo[9.2.1.02,7.03,5.04,8.09,13]tetra­decane with sodium hydroxide in n-butanol afforded 10-exo-aminohexacyclo[9.2.1.02,7.03,5.04,8.09,13]tetradecane in quantitative yield.