Synthesis of Homoallylic Amines via 2-Aza-Cope Rearrangement

Abstract

The enantioselective transfer amino­allylation catalyzed by a Brønsted acid leading to homoallylic primary amines 6 is described. Starting from aldehyde 1 and chiral homoallylamine 2, an imine-intermediate 3 is formed, which can undergo a 2-aza-Cope rearrangement to imine 4. Finally, the homoallylic amine 6 is released after cleavage of the imine bond with hydroxylamine. The authors have employed camphorsulfonic acid as a catalyst, leading to homoallylic amines 6 in good yields and excellent enantiomeric ratios.