Borylated oximes: versatile building blocks for organic synthesis†
Sean K.
Liew, 
a
Aleksandra
Holownia,
a
Diego B.
Diaz,
a
Philip A.
Cistrone,
b
Philip E.
Dawson
b
and
Andrei K.
Yudin
*a
a
Aleksandra
Holownia,
a
Diego B.
Diaz,
a
Philip A.
Cistrone,
b
Philip E.
Dawson
b
and
Andrei K.
Yudin
*a
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.
- This article is part of the themed collection: Site-selective molecular transformations
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