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

Abstract

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

Key words

C–N bond cleavage - oxidation - cyclic amines - ammonium hypochlorite - amino acids

Publication History

Received: 31 January 2023

Accepted after revision: 27 March 2023

Accepted Manuscript online:
27 March 2023

Article published online:
24 April 2023

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