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

Abstract

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.