Discrimination of stereoisomers by one-dimensional 13 C NMR: All 16 stereoisomers of 4-hydroxy-α-tocopherol resolved.

All 16 resolved! A vitamin E-derived compound containing four chiral centers is the first example where all stereoisomers, that is, eight diastereomeric pairs of enantiomers, could be discriminated in a single NMR run. Measurement at 176 MHz in the presence of Pirkle's alcohol as a chiral solvating agent is a relatively robust, simple, easy-to-set-up, and fast method.