Development of New Reactions Driven by N-O Bond Cleavage: from O -Acyl Hydroxylamines to Tetrodotoxin.

Published in: Synlett : accounts and rapid communications in synthetic organic chemistry (2023)

This Account describes new reactions that have been developed in the Johnson laboratories at UNC Chapel Hill enabled by considerations of N-O bond cleavage. Three main case studies are highlighted: the metal-catalyzed electrophilic amination of O -acyl hydroxyl amines, multihetero-Cope rearrangements driven by O-N bond breakage, and merged dearomatization/N=O cycloadditions for the synthesis of complex 4-aminocyclohexanols such as those found in the natural product tetrodotoxin.

Keyphrases

dna binding
fatty acid
transition metal
room temperature
electron transfer