2,6-Bis(trifluoromethyl)phenylboronic Esters as Protective Groups for Diols: A Protection/Deprotection Protocol for Use under Mild Conditions
journal contribution
posted on 2018-09-18, 20:15 authored by Naoyuki Shimada, Sari Urata, Kenji Fukuhara, Takao Tsuneda, Kazuishi MakinoThe application of
2,6-bis(trifluoromethyl)phenyl boronic acid
(<i>o</i>-FXylB(OH)<sub>2</sub>; <i>o</i>-FXyl
= 2,6-(CF<sub>3</sub>)<sub>2</sub>C<sub>6</sub>H<sub>3</sub>) as a
recoverable and reusable protective agent for diols is described.
The resulting cyclic boronic esters are water- and air-stable and
tolerant to various organic transformations. Moreover, they can be
deprotected under mild conditions. This methodology was applied to
the synthesis of a highly conjugated enetriyne natural product with
anti-angiogenic activities.
