Enantoioselective reactions of some optically active phosphines.

The enantioselective chlorination of alcohols by the menthyldipheny1-phosphine/carbon tetrachloride reagent previously reported in the literature was investigated and quantified. Further examples were found. A new enantioselective reaction of menthyldipheny1phosphine/carbon tetrachloride was discovered. This was the synthesis of aziridines by ring closure of ? amino alcohols. Other optically active phosphines in conjunction with carbon tetrachloride were found to react in a similar manner to menthy1dipheny1phosphine/carbon tetrachloride with a variety of ? amino alcohols. Menthy1dipheny1phosphine was found to react enantioselectively with a ? amino alcohol in the presence of chlorine.