Crystallization-Induced Dynamic Resolution of Fox Chiral Auxiliary and Application to the Diastereoselective Electrophilic Fluorination of Amide Enolates

Abstract

A highly efficient crystallization-induced dynamic resolution (CIDR) of <i>trans</i>-<b>Fox</b> (fluorinated oxazolidine) chiral auxiliary is reported. This chiral auxiliary was used for highly diastereoselective (>98% <i>de</i>) electrophilic fluorination of amide enolates. After removal of the chiral auxiliary, highly valuable enantiopure α-fluorocarboxylic acids and β-fluoroalcohols are obtained