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Synthesis and Stability of Asparagine-Derived N,N´–Amidals and N,N´–Hemiamidals

14 October 2025, Version 1
Working Paper
This content is an early or alternative research output and has not been peer-reviewed by Cambridge University Press at the time of posting.

Abstract

We report modular syntheses of asparagine-derived hemiamidals, amidals, and protected variants via their corresponding isocyanates. Stability studies of the hemiamidals provide key insights for the application of these emerging functional groups in conditional activation chemistry and as final products. These findings have direct relevance for the design of small molecule prodrugs and cleavable linkers.

Keywords

amidals
Curtius Rearrangement
amides

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Version History

Oct 14, 2025 Version 1

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The content is available under CC BY 4.0 [opens in a new tab]

DOI

10.26434/chemrxiv-2025-8fpxz
D O I: 10.26434/chemrxiv-2025-8fpxz [opens in a new tab]

Author’s competing interest statement

The author(s) have declared they have no conflict of interest with regard to this content

Ethics

The author(s) declare that they have sought and gained approval from the relevant ethics committee/IRB for this research and its publication.

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