m-Terphenyl Ethers, a New Hydroxy Protecting Group Cleavable under Reductive Single Electron Transfer Reaction Conditions
作者:Ugo Azzena、Luisa Pisano、Sarah Mocci
DOI:10.1055/s-0030-1259997
日期:2011.5
m-Terphenyl ethers and, to a lesser extent, 2,6-dimethoxyphenyl ethers, were tested as protected hydroxy derivatives under a variety of reaction conditions. These ethers underwent regioselective cleavage of the aromatic C(1)-O bond under reductive SET reaction conditions using alkali metals in tetrahydrofuran at room temperature. This deprotective procedure was efficiently realized in the presence
have investigated the regio- and stereochemistry of the reductive dealkoxylation of alkyl aryl ethers. Chiral non-racemic secondary alcohols were converted into the corresponding m-terphenyl or 2-biphenyl ethers either via inversion of configuration under Mitsunobu reaction conditions or with retention of configuration under SNAr conditions. The successive cleavage of the aromatic CO bond occurred