Synthesis of Rosin Derived Chiral derivatizing agents for31P NMR assays of amine or alcohol and amino alcohol enantiomers

Chiral alcohols 3 and 6 were synthesized in optically pure forms from easily available rosin acid in short-steps. A comprehensive protocol for the enantiomeric excess assays of monoor di-functional-grouped chiral secondary amine or alcohol has been established by using them as chiral auxiliary for chiral phosphorus derivatizing reagents (CPDA) in P NMR tests. Chemical shift difference (Δδp) values ranging from 3.08 to 0.10 between two diastereoisomers of the CPDAs and the aryl substrates were obtained. The enantiomeric excess of 1-(1-naphthyl)ethylamine and 1,1'-bi(2-naphthol) is determined using our CPDA, and the results showed that the relative error was less than ±2%.