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

Abstract

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.

1 Introduction

2 Electrophilic Amination

3 Multihetero-Cope Rearrangements

4 Progress toward a Total Synthesis of (–)-Tetrodotoxin

5 Conclusion

Key words

amination - catalysis - sigmatropic reactions - total synthesis - tetrodotoxin - cycloadditions

Publication History

Received: 13 January 2023

Accepted: 24 January 2023

Article published online:
23 February 2023

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