Borylated oximes: versatile building blocks for organic synthesis

作者：Liew Sean K; Holownia Aleksandra; Diaz Diego B; Cistrone Philip A; Dawson Philip E; Yudin Andrei K^*

来源：Chemical communications, 2017, 53(81): 11237-11240.

DOI：10.1039/c7cc06579e

Herein, we demonstrate the synthesis and functionalization of alpha-boryl aldoximes from alpha-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 alpha-boryl aldoximes, MIDA deprotection yields the corresponding beta-boryl hydroxylamines. As part of this study, we also demonstrate the utility of the boryl aldoxime motif in peptide conjugation.

• 出版日期2017-10-18