Derivatizing agents from phosphorus trichloride and terpenyl tartrates for determining the enantiomeric purity of alcohols

Heterocyclic phosphorous acid chlorides, prepared from C₂-symmetric menthyl, borneyl, or fenchyl tartrates and phosphorus trichloride, are inexpensive derivatizing agents for determining the enantiomeric purity of alcohols via phosphorus NMR. The most versatile agent identified from this study, a (1R,2S,5R)-menthyl (R,R)-tartrate-derived 2-chloro-1,3,2-dioxaphospholane, gives, upon esterification with chiral alcohols, diastereomeric phosphites showing phosphorus NMR-shift dispersions between 0.1 ppm and 1.5 ppm.