z-logo
Premium
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.

This content is not available in your region!

Continue researching here.

Having issues? You can contact us here