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Optical resolution of 1‐(1‐naphthyl)ethylamine by its dicarboxylic acid derivatives: Structural features of the oxalic acid derivative diastereomeric salt pair
Author(s) -
Bereczki Laura,
Bombicz Petra,
Bálint József,
Egri Gabriella,
Schindler József,
Pokol György,
Fogassy Elemér,
Marthi Katalin
Publication year - 2009
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.20535
Subject(s) - ethylamine , chemistry , diastereomer , enantiomer , dicarboxylic acid , chirality (physics) , stereochemistry , oxalic acid , derivative (finance) , chiral resolution , crystal structure , succinic acid , malonic acid , glutaric acid , resolution (logic) , crystallography , organic chemistry , chiral symmetry , physics , quantum mechanics , artificial intelligence , computer science , financial economics , nambu–jona lasinio model , economics , quark
Optical resolution methods were established for racemic 1‐(1‐naphthyl) ethylamine. The resolving agents were synthesized by N ‐derivatizing ( R )‐1‐(1‐naphthyl) ethylamine with dicarboxylic acids. Oxalic, malonic, and succinic acid derivatives were found to be suitable resolving agents. These resolutions are parallel to a series of optical resolutions of 1‐phenylethylamine which had been previously performed by our research group using similar derivative resolving agents (Balint et al., Tetrahedron: Asymmetry 2001;12:1511–1518.) The comparison of the results of the enantiomer separations is performed. The diastereomeric salts formed with ( R )‐ N ‐[1‐(1‐naphthyl)ethyl]oxalamic acid were investigated by single crystal X‐ray diffraction. The crystal structures were compared with the previously published structures of the diastereomers of the phenyl‐substituted analogue, namely ( R )‐ and ( S )‐1‐phenylethylammonium ( R ) ‐N ‐(1‐phenylethyl)oxalamates (Balint et al., Tetrahedron: Asymmetry 2001;12:1511–1518.) Chirality, 2009. © 2008 Wiley‐Liss, Inc.