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Synlett 2023; 34(13): 1563-1572
DOI: 10.1055/s-0042-1751423
DOI: 10.1055/s-0042-1751423
account
Development of New Reactions Driven by N–O Bond Cleavage: from O-Acyl Hydroxylamines to Tetrodotoxin
The project described was supported by award no. R35 GM118055 from the National Institute of General Medical Sciences.
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 - cycloadditionsPublikationsverlauf
Eingereicht: 13. Januar 2023
Angenommen: 24. Januar 2023
Artikel online veröffentlicht:
23. Februar 2023
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