Determination of the absolute configuration and enantiomeric purity of chiral primary alcohols by 1H NMR of 9-anthrylmethoxyacetates

• Published in: Tetrahedron: asymmetry Vol. 7; no. 8; pp. 2195 - 2198
• Main Authors: Ferreiro, M.J., Latypov, Sh.K., Quiñoá, E., Riguera, R.
• Format: Journal Article
• Language: English
• Published: Elsevier Ltd 01-08-1996
• ISSN: 0957-4166; 1362-511X
• DOI: 10.1016/0957-4166(96)00269-8

The absolute configuration and e.e. of chiral primary alcohols with the asymmetric centre at the β carbon can be determined by comparison of the
1H NMR spectra of their esters with (
R)- and (
S)-9-anthrylmethoxyacetic acids (9-AMA). Highly hindered primary alcohols or primary alcohols with the asymmetric centre at longer distance from the hydroxy group can hardly be determined by this method that is nevertheless highly useful for e.e. determination.
The absolute configuration and e.e. of chiral primary alcohols with the asymmetric centre at the β carbon can be determined by comparison of the
1H NMR spectra of the esters of (
R)- and (
S)-9-anthrylmethoxyacetic acids (9-AMA).