An effective and useful synthesis of enantiomerically enriched arylglycinols

A two-step synthesis of racemic arylglycinols, together with a simple and s traightforward methodology for their resolution, is described. This method constitutes a practical means of preparing racemic and optically pure elect ron-rich or electron-poor substituted arylglycinols, useful building blocks for the synthesis of biologically active molecules and chiral ligands. All of the chiral beta -amino alcohols 5-8 were isolated in good chemical yiel ds and with excellent enantiomeric excesses: up to 99% in the cases of the arylglycinols 7 and 8. Chiral fluoroaromatic vicinal amino alcohols can als o be obtained with good enantiopurity using such a procedure. The key step of the strategy presented is an easy chromatographic separation of the dias tereoisomeric amides prepared from acetyl mandeloyl chloride. The absolute configuration of the perfluorinated amino alcohols 5 was determined by X-ra y analysis of the corresponding amide 14a.