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Substituent effects on chiral resolutions of derivatized 1‐phenylalkylamines by heptakis(2,3‐di‐ O ‐methyl‐6‐ O ‐ tert ‐butyldimethylsilyl)‐β‐cyclodextrin GC stationary phase
Author(s) -
Issaraseriruk Natthapol,
Sritanaanant Yongsak,
Shitangkoon Aroonsiri
Publication year - 2018
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.22856
Subject(s) - chemistry , substituent , enantiomer , ethylamine , stereocenter , gas chromatography , chiral column chromatography , stereochemistry , medicinal chemistry , chromatography , organic chemistry , enantioselective synthesis , catalysis
Chiral resolutions of trifluoroacetyl‐derivatized 1‐phenylalkylamines with different type and position of substituent were investigated by capillary gas chromatography by using heptakis(2,3‐di‐ O ‐methyl‐6‐ O ‐ tert ‐butyldimethylsilyl)‐ β ‐cyclodextrin diluted in OV‐1701 as a chiral stationary phase. The influence of column temperature on retention and enantioselectivity was examined. All enantiomers of meta ‐substituted analytes as well as fluoro‐substituted analytes could be resolved. Temperature had a favorable influence on enantioselectivity for small amines with substituents at the ortho ‐position. The type of substituent at the stereogenic center of amines also had a crucial effect as the ethyl group led to poor enantioseparation. Among all analytes studied, trifluoroacetyl‐derivatized 1‐(2′‐fluorophenyl)ethylamine exhibited baseline resolution with the shortest analysis time.