In situ synthesis of rosin derived chiral derivatizing agents for 31 P NMR assays of amine and alcohol enantiomers

Chiral alcohols( 3 , 5 ) were synthesized in optically pure forms from easily available rosin acid in short-steps. A comprehensive protocol for the enantiomeric excess assays of mono-or di-functional-grouped chiral secondary amine or alcohol has been established with them used as chiral auxiliary for chiral phosphorus derivatizing agents(CPDAs) in 31 P NMR tests. Chemical shift difference(Δ δ P ) values ranging from 4.5 to 0.15 between two diastereoisomers of the CPDAs and the aryl substrates were obtained. Positive Δ δ R-S was observed for all the tested alcohol P(III) and P(V) derivatives, while negative Δ δ R-S was observed for all the amines.