Oxidative Rearrangement via in Situ Generated N-Chloroamine: Synthesis of Fused Tetrahydroisoquinolines

An oxidative rearrangement reaction of spiro tetrahydroisoquinolines has been developed for the synthesis of fused tetrahydroisoquinolines using in situ generated N-chloroamines. The reaction proceeds via initial chlorination of an amine, followed by a 1,2-carbon to nitrogen migration, and nucleophilic trapping of a ketiminium ion intermediate in a one-pot operation. The electrophilic nature of N-chloroamines allowed for the carbon nitrogen bond formation in this reation.