Borylated oximes: versatile building blocks for organic synthesis
Literature Information
Sean K. Liew, Aleksandra Holownia, Diego B. Diaz, Philip A. Cistrone, Philip E. Dawson, Andrei K. Yudin
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.
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