Artigo Acesso aberto Produção Nacional Revisado por pares

Limitations in determining enantiomeric excess of alcohols by 31P-NMR of the phosphonate derivatives

1999; Brazilian Chemical Society; Volume: 10; Issue: 4 Linguagem: Inglês

10.1590/s0103-50531999000400007

ISSN

1678-4790

Autores

Antônio Laverde, Domingos S. de Miranda, Gelson José Andrade da Conceição, Heiko Schirmer, Ronaldo A. Pilli, Armin de Meijere, Anita J. Marsaioli,

Tópico(s)

Analytical Chemistry and Chromatography

Resumo

The use of diastereomeric alcohol dialkylphosphonate derivatives to determine the enantiomeric excesses via 31P-NMR signal ratios of anisochronous meso and threo isomers was successfully applied to secondary alcohols (Feringa’s method). Expansion of the methodology to primary alcohols possessing the hydroxyl groups thethered to the stereogenic centers by two or more methylene groups proved the method to be inefficent. The comparison between the coupled and decoupled spectra is important in order to identify the signals corresponding to the dialkylphosphonates. Nevertheless the methodology should be applied whenever the amount of the alcohol and its structure are not the limiting factors.

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