Double Nucleophilic Addition of Azide and Tetramethallyltin to (alpha),(beta)-Unsaturated Aldimines Promoted by Aluminum Chloride

In the presence of AlCl3, a mixture of hydrogen azide and tetramethallyltin underwent 1,4- and subsequently 1,2-addition, respectively, with (alpha),(beta)-unsaturated aldimines to give 1,3-amino azides in good yields. The 1,3-amino azides thus obtained were readily converted into 1,3-diamines by reduction with LiAlH4.