Stereoselective reactions with imines

Abstract

By the activation of general imines or using activated imines (N-tosylimines or N-diphenyl-phosphinoylimines), we developed three types of stereoselective reactions with imines: aldol reaction, allylation, and aziridiantion, and optically active 2-imidazolines and aziridines were obtained. According to experimental evidences, Sakurai-Hosomi reactions in the presence of catalytic amount of TBAF was demonstrated to be a fluoride-triggered autocatalytic mechanism. In addition, optically active 2,3-diamino acids were also synthesised conveniently by chemical transformations of 2-imidazolines. © 1999 IUPAC.