PREPARATION OF CHIRAL PHOSPHORUS, SULFUR AND SELENIUM-CONTAINING 2-ARYLOXAZOLINES

A series of enantiomerically pure 2-(2-(diarylphosphino)aryl]-oxazolin es was prepared from commercially available or synthetic amino alcohol s. For oxazoline formation three procedures were employed: (i) one pot condensation with a 2-halobenzoic acid, (ii) ZnCl2 catalyzed condensa tion with a 2-halobenzonitrile, and (iii) a three step sequence via a 2-halobenzamide and a tosylate or chloride. Phosphinooxazolines contai ning stereogenic phosphorus were prepared by either diastereoselective nucleophilic substitution of halogenide of (ArArPCl)-Ar-1-P-2 or by n ucleophilic aromatic substitution with (LiPArAr2)-Ar-1. In addition, s ulfur and selenium analogs were prepared. Copyright (C) 1996 Elsevier Science Ltd