Oxidative C-N Bond Cleavage of Cyclic Amines with Ammonium Hypochlorite

An oxidative C-N bond cleavage of cyclic amines has been developed under metal-free conditions, providing N-Cl-?-amino acids in moderate to excellent yields. The reactions proceed by using tetramethylammonium hypochlorite (TMAOCl) as an oxidant even on a gram scale. Hofmann-Loffler-Freytag-type reaction of N-Cl-?-amino acids to form cyclic amino acids has also been demonstrated.

Automated summary

A metal-free oxidative C-N bond cleavage of cyclic amines has been developed to provide N-Cl-?-amino acids in moderate to excellent yields. The reactions can proceed even on a gram scale using tetramethylammonium hypochlorite (TMAOCl) as an oxidant. Furthermore, the Hofmann-Loffler-Freytag-type reaction of N-Cl-?-amino acids to form cyclic amino acids has been demonstrated.