Synthesis of [2.2]Paracyclophane‐Based Glycidic Amides Using Chiral Ammonium Ylides

Abstract

AbstractAn ammonium ylide‐mediated stereoselective protocol for the synthesis of a series of novel [2.2]paracyclophane‐based epoxides starting from racemic 4‐formyl[2.2]paracyclophane has been developed. By using achiral ammonium salts as ylide precursors, the corresponding epoxide products were obtained in isolated yields up to 76 % and with diastereoselectivities up to d.r.=9 : 1. When carrying out the reaction with chiral ammonium salts instead, the products were accessible with e.r.>93.5 : 6.5 and d.r.>3 : 1, accompanied with a moderately enantioselective kinetic resolution of the racemic starting aldehyde (e.r.=75 : 25).