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New chiral fluoroanthryl derivatives: Resolution of the enantiomers by chromatography on cellulose esters and their evaluation as chiral solvating agents in NMR spectroscopy
Author(s) -
Francotte Eric,
Lang Robert W.,
Winkler Tammo
Publication year - 1991
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.530030307
Subject(s) - chemistry , enantiomer , cellulose , chiral derivatizing agent , resolution (logic) , nuclear magnetic resonance spectroscopy , chiral column chromatography , organic chemistry , chiral resolution , spectroscopy , chromatography , combinatorial chemistry , computational chemistry , physics , quantum mechanics , artificial intelligence , computer science
Abstract 2,2,2‐Trifluoro‐1‐(9‐anthryl)ethanol (TFAE) has now been widely used as a powerful chiral solvating agent for NMR spectroscopy. In connection with the development of a new general synthesis of halogenoalkylalkanols, starting from the corresponding ketone or aldehyde, we synthesized some halogenoalkyl‐1‐(9‐anthryl)methanol derivatives liable to work as chiral solvating agents. The racemic anthryl derivatives were preparatively resolved into their corresponding enantiomers by chromatography on triacetyl cellulose (CTA I) or on meta ‐methylbenzoyl cellulose beads as chiral stationary phases. Their effectiveness as chiral solvating agents was measured as the magnitude of the splitting induced in the 1 H‐NMR spectra of 1‐phenylethylamine and of (1‐phenylethyl)methyl ether in comparison with splitting caused by TFAE. While TFAE induced the largest splitting for 1‐phenylethylamine, 2,2,3,3,3‐pentafluoro‐1‐(9‐anthryl)propanol 2 was more effective in the case of (1‐phenylethyl)methyl ether, pointing out that depending on the substrate, other derivatives of the TFAE type can be very useful as chiral solvating agents.