Regioselective Side-Chain Amination Of 2-Alkyl Azacycles By Radical Translocation: Total Synthesis Of Tetraponerine T8

The regioselective gamma-C-H amination of the side-chain of saturated 2-alkyl nitrogen heterocycles is reported, proceeding through a sulfamide-directed 1,6-radical translocation. The practicality of this rapid access to 1,3-diamines is highlighted in a short synthesis of the alkaloid tetraponerine T8 and non-natural analogues.