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Issue 81, 2017
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Borylated oximes: versatile building blocks for organic synthesis

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Abstract

Herein, we demonstrate the synthesis and functionalization of α-boryl aldoximes from α-boryl aldehydes, with no sign of C-to-N boryl migration. Selective modification of the oxime functionality enables access to a wide range of borylated compounds, such as borylated heterocycles and N-acetoxyamides. By reducing the α-boryl aldoximes, MIDA deprotection yields the corresponding β-boryl hydroxylamines. As part of this study, we also demonstrate the utility of the boryl aldoxime motif in peptide conjugation.

Graphical abstract: Borylated oximes: versatile building blocks for organic synthesis

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Publication details

The article was received on 22 Aug 2017, accepted on 04 Sep 2017 and first published on 11 Sep 2017


Article type: Communication
DOI: 10.1039/C7CC06579E
Citation: Chem. Commun., 2017,53, 11237-11240
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    Borylated oximes: versatile building blocks for organic synthesis

    S. K. Liew, A. Holownia, D. B. Diaz, P. A. Cistrone, P. E. Dawson and A. K. Yudin, Chem. Commun., 2017, 53, 11237
    DOI: 10.1039/C7CC06579E

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