2,6-Bis(trifluoromethyl)phenylboronic Esters as Protective Groups for Diols: A Protection/Deprotection Protocol for Use under Mild Conditions
journal contributionposted on 18.09.2018 by Naoyuki Shimada, Sari Urata, Kenji Fukuhara, Takao Tsuneda, Kazuishi Makino
Any type of content formally published in an academic journal, usually following a peer-review process.
The application of 2,6-bis(trifluoromethyl)phenyl boronic acid (o-FXylB(OH)2; o-FXyl = 2,6-(CF3)2C6H3) 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.