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2,6-Bis(trifluoromethyl)phenylboronic Esters as Protective Groups for Diols: A Protection/Deprotection Protocol for Use under Mild Conditions

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journal contribution
posted on 18.09.2018, 20:15 authored by Naoyuki Shimada, Sari Urata, Kenji Fukuhara, Takao Tsuneda, Kazuishi Makino
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.