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Phenylglycine Methyl Ester, a Useful Tool for Absolute Configuration Determination of Various Chiral Carboxylic Acids

1999; American Chemical Society; Volume: 65; Issue: 2 Linguagem: Inglês

10.1021/jo991218a

1520-6904

Tetsuya Yabuuchi, Takenori Kusumi,

Metabolomics and Mass Spectrometry Studies

A new chiral anisotropic reagent, phenylglycine methyl ester (PGME), developed for the elucidation of the absolute configuration of chiral alpha,alpha-disubstituted acetic acids, has turned out to be applicable to other substituted carboxylic acids, such as chiral alpha-hydroxy-, alpha-alkoxy-, and alpha-acyloxy-alpha, alpha-disubstituted acetic acids, as well as to chiral beta, beta-disubstituted propionic acids. Because a carboxylic moiety is convertible from other functional groups, e.g., ozonolysis of an olefin and oxidative cleavage of a glycol, the present findings can expand the utility of the PGME method to the absolute configuration determination of various types of organic compounds, even those which initially lack oxygen functions. Several examples of the combination of chemical reactions and the PGME method are described.