A number of chiral 1-arylethylamines and 1-alkylethylamines were resolved with the 3-carboxy-2-naphthoate of isopropylidene glycerol 2, previously reported to be an even more efficient resolving agent for 1-phenylethylamine than the corresponding hemiphthalate 1. The results obtained for the 1-arylethylamines confirm such a trend, revealing impressive resolution ability, in particular, for 1-(4-bromophenyl)-, 1-(4-nitrophenyl)- and 1-(2-naphthyl)ethylamine, whose enantiomers were almost quantitatively separated with (S)-2 by a single precipitation of the less soluble (S,S) diastereomeric salt. Additionally, the success of the resolutions of 1-alkylethylamines (1-phenyl-2-propylamine, 1-cyclohexylethylamine and 2-butylamine), which could not be resolved with 1, indicates that the novel carboxy ester 2 has a wider range of application than 1.
Highly efficient resolutions with isopropylidene glycerol 3-carboxy-2-naphthoate / M. Pallavicini, C. Bolchi, L. Fumagalli, E. Valoti, L. Villa. - In: TETRAHEDRON-ASYMMETRY. - ISSN 0957-4166. - 13:20(2002), pp. 2277-2282. [10.1016/S0957-4166(02)00608-0]
Highly efficient resolutions with isopropylidene glycerol 3-carboxy-2-naphthoate
M. Pallavicini;C. Bolchi;L. Fumagalli;E. Valoti;
2002
Abstract
A number of chiral 1-arylethylamines and 1-alkylethylamines were resolved with the 3-carboxy-2-naphthoate of isopropylidene glycerol 2, previously reported to be an even more efficient resolving agent for 1-phenylethylamine than the corresponding hemiphthalate 1. The results obtained for the 1-arylethylamines confirm such a trend, revealing impressive resolution ability, in particular, for 1-(4-bromophenyl)-, 1-(4-nitrophenyl)- and 1-(2-naphthyl)ethylamine, whose enantiomers were almost quantitatively separated with (S)-2 by a single precipitation of the less soluble (S,S) diastereomeric salt. Additionally, the success of the resolutions of 1-alkylethylamines (1-phenyl-2-propylamine, 1-cyclohexylethylamine and 2-butylamine), which could not be resolved with 1, indicates that the novel carboxy ester 2 has a wider range of application than 1.Pubblicazioni consigliate
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