Enamine N-oxides: Design, Synthesis, and Function in Bioorthogonal Reactions
Dahye Kang1,2, Justin Kim1,2
1Department of Cancer Biology, Dana-Farber Cancer Institute, Boston, Massachusetts 02215, United States.
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.
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