Journal
CHEMICAL SCIENCE
Volume 5, Issue 11, Pages 4328-4332Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c4sc00971a
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Funding
- ETH-Zurich
- ETH Grant [ETH 43 13-2]
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N-Methyliminodiacetyl (MIDA) acylboronates undergo chemoselective amide-bond forming ligations in water with O-Me hydroxylamines, including unprotected peptide substrates. These bench-stable boronates were easily prepared from potassium acyltrifluoroborates (KATs) in one step. The reactivity of MIDA acylboronates with O-alkylhydroxylamines - which are unreactive with KATs - was attributed to the nature of the neutral MIDA boronates versus the ionic KATs, leading to differences in the stability of likely intermediates and propensity for elimination.
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