An effective and useful synthesis of enantiomerically enriched arylglycinols

A two-step synthesis of racemic arylglycinols, together with a simple and straightforward methodol. for their resoln., is described. This method constitutes a practical means of prepg. racemic and optically pure electron-rich or electron-poor substituted arylglycinols, useful building blocks for the synthesis of biol. active mols. and chiral ligands. All of the chiral beta-amino alcs. were isolated in good chem. yields and with excellent enantiomeric excesses. Chiral fluoroarom. vicinal amino alcs. can also be obtained with good enantiopurity using such a procedure. The key step of the strategy presented is an easy chromatog. sepn. of the diastereoisomeric amides prepd. from acetyl mandeloyl chloride. The abs. configuration of the perfluorinated amino alcs. was detd. by X-ray anal. of the corresponding amide.