Preparation of chiral phosphorus, sulfur and selenium containing 2-aryloxazolines

Article abstract of DOI:10.1016/0040-4020(96)00267-0

A series of enantiomerically pure 2-[2-(diarylphosphino)aryl]-oxazolines was prepared from commercially available or synthetic amino alcohols. For oxazoline formation three procedures were employed: (i) one pot condensation with a 2-halobenzoic acid (ii) ZnCl₂ catalyzed condensation with a 2-halobenzonitrile, and (iii) a three step sequence via a 2-halobenzamide and a tosylate or chloride. Phosphinooxazolines containing stereogenic phosphorous were prepared by either diastereoselective nucleophilic substitution of halogenide of Ar¹Ar²PCl or by nucleophilic aromatic substitution with LiPAr¹Ar². In addition, sulfur and selenium analogs were prepared.