Abstract
Enamine N-oxides act as a chemical linchpin bridging two bioorthogonal associative and dissociative reactions. This article describes the design of enamine N-oxides, their synthesis through the retro-Cope elimination reaction, the use of solvent, hyperconjugation, strain, and rehybridization effects to achieve bioorthogonal reactivity, and their rapid reductive cleavage with diboron reagents. The coordinated assembly and disassembly of the enamine N-oxide motif constitutes a powerful chemical operation that enables the attachment and detachment of small molecules from biomacromolecules in a biological setting.
1 Introduction
2 Background
3 General Access to Linear Enamine N-Oxides
4 Strain-Promoted Hydroamination Reaction
5 Electronically Activated Alkynes
6 Chemically Revertible Reactions
7 Conclusion
Key words
bioorthogonal chemistry - enamine
N-oxides - ligation reaction - cleavage reaction - strain-promoted reaction - rehybridization effect - diboron
