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The use of ethyl 2-(9-anthryl)-2-hydroxyacetate for assignment of the absolute configuration of carboxylic acids by 1H NMR

✍ Scribed by María J. Ferreiro; Shamil K. Latypov; Emilio Quiñoá; Ricardo Riguera

Publisher
Elsevier Science
Year
1997
Tongue
English
Weight
241 KB
Volume
8
Category
Article
ISSN
0957-4166

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✦ Synopsis

Both theoretical and experimental evidences prove that the absolute configuration of an et-chiral carboxylic acid can be safely assigned by comparison of the 1H NMR spectra of its esters with (R)-and (S)-ethyl 2-(9-anthryl)-2-hydroxyacetate (5, AHA). A simplified conformational model, based on the dominance of the ap over the sp conformer and the selective effect of the anthryl group, allows the (R/S) assignment directly from the NMR chemical shifts.

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## Abstract Racemic 1‐ and 2‐naphthylmethoxyacetic acids (1NMA and 2NMA), the chiral anisotropic reagents used for absolute configuration determination of chiral secondary alcohols and primary amines, were conveniently resolved to enantiomers (>99% ee) by condensation with L‐phenylalaninol (2‐amino