Abstract—The hydrogen phthalate of isopropylidene glycerol 1, previously reported as an efficient resolving agent of p-substituted 1-phenylethylamines, was also found to resolve selected o- and m-isomers. In particular, the (S)-enantiomers of 1-(2- methylphenyl)ethylamine 2, 1-(3-methylphenyl)ethylamine 3, 1-(2-chlorophenyl)ethylamine 4 and 1-(3-methoxyphenyl)ethylamine 5 were obtained in good yields and very high enantiomeric excess (e.e.) by selective crystallization of the respective salts with (S)- or (R)-1. The e.e.s of the resolved substrates were determined by chiral HPLC analysis. The (S)-configuration of (−)-3 was established according to Raban’s procedure. Optical rotations of non-racemic free amines 2 and 3 are reported. The success of the resolutions presented and of the precedent ones using 1 indicate that the position of the substituent on the 1-phenylethylamine framework does not affect the resolution, showing the uncommon versatility of 1 in the resolution of monosubstituted 1-phenylethylamines.
|Titolo:||Resolution of ortho- and meta-substituted 1-phenylethylamines with isopropylidene glycerol|
PALLAVICINI, MARCO (Primo)
VALOTI, ERMANNO (Secondo)
|Settore Scientifico Disciplinare:||Settore CHIM/06 - Chimica Organica|
|Data di pubblicazione:||2001|
|Digital Object Identifier (DOI):||10.1016/S0957-4166(01)00156-2|
|Appare nelle tipologie:||01 - Articolo su periodico|