Regioselective side-chain amination of 2-alkyl azacycles by radical translocation: total synthesis of tetraponerine T8

Abstract

The regioselective γ-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.