Borylated oximes: versatile building blocks for organic synthesis

Literature Information

Publication Date 2017-09-11
DOI 10.1039/C7CC06579E
Impact Factor 6.222
Authors

Sean K. Liew, Aleksandra Holownia, Diego B. Diaz, Philip A. Cistrone, Philip E. Dawson, Andrei K. Yudin


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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.

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