Enantiomeric excess detection with (S)-3-Phenyl-2-(selenophenyl)propan-1-ol derivatizing agent via mix and shake 77Se NMR

Abstract

In this article, we demonstrate that (S)-3-phenyl-2-(selenophenyl)propan-1- ol can be successfully employed as chiral derivatizing agent for enantiomeric excess determination of chiral carboxylic acid substrates via 77Se NMR. The required derivatives are obtained by mixing the chiral derivatizing agent with the non racemic carboxylic acid substrate directly in the NMR tube and determining the enantiomeric excess with just one spectrum. The best results were obtained with (S)-3-phenyl-2- (selenophenyl)propan-1-ol, which showed good anysochronies of the selenium signals, ranging from Δδ = 22 Hz to Δδ = 211 Hz, even with the stereocenter and the selenium atom five bonds apart. © 2010 Sociedade Brasileira de Química.