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

Abstract

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 ³¹P NMR tests. Chemical shift difference(Δδ _P) values ranging from 4.5 to 0.15 between two diastereoisomers of the CPDAs and the aryl substrates were obtained. Positive Δδ _R-S was observed for all the tested alcohol P(III) and P(V) derivatives, while negative Δδ _R-S was observed for all the amines.

Keywords

Chiral phosphorus derivatizing agent / Rosin / Enantiodiscrimination / ³¹P NMR

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