10.1021/acs.orglett.8b02427.s001 Naoyuki Shimada Naoyuki Shimada Sari Urata Sari Urata Kenji Fukuhara Kenji Fukuhara Takao Tsuneda Takao Tsuneda Kazuishi Makino Kazuishi Makino 2,6-Bis(trifluoromethyl)phenylboronic Esters as Protective Groups for Diols: A Protection/Deprotection Protocol for Use under Mild Conditions American Chemical Society 2018 agent anti-angiogenic activities Ester acid Diol methodology Mild Conditions application Protection enetriyne deprotected Bis synthesis diol FXylB bi 2 C 6 H 3 CF cyclic boronic esters FXyl air-stable Protective Groups transformation 2018-09-18 20:15:20 Journal contribution https://acs.figshare.com/articles/journal_contribution/2_6-Bis_trifluoromethyl_phenylboronic_Esters_as_Protective_Groups_for_Diols_A_Protection_Deprotection_Protocol_for_Use_under_Mild_Conditions/7100675 The 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.