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Achiral derivatization as a means of improving the chromatographic resolution of racemic alcohols on benzoylcellulose CSPs
Author(s) -
Francotte Eric
Publication year - 1998
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/(sici)1520-636x(1998)10:5<492::aid-chir12>3.0.co;2-v
Subject(s) - chemistry , derivatization , enantiomer , substituent , cellulose , selectivity , organic chemistry , chirality (physics) , enantiomeric excess , chromatography , combinatorial chemistry , enantioselective synthesis , high performance liquid chromatography , catalysis , chiral symmetry breaking , physics , quantum mechanics , nambu–jona lasinio model , quark
The advantages that can be gained from derivatization of various racemic aliphatic and aromatic alcohols prior to enantiomeric chromatographic separation have been systematically investigated for a series of benzoate derivatives. Three cellulose‐based CSPs available in the pure polymeric form—tribenzoyl cellulose (TBC), meta ‐methylbenzoyl cellulose (MMBC), and para ‐methylbenzoyl cellulose (PMBC)—were selected and several benzoate derivatives varying in the nature and the position of the substituent on the benzoyl group were prepared and analysed. TBC clearly gives the broadest application range, and among the different benzoate esters the best selectivity was generally obtained with either the 4‐methoxybenzoate or the 4‐methylbenzoate derivatives. Based on these results, some empirical rules could be formulated for optimizing the enantiomeric separation of racemic alcohols, which make up one of the most important classes of chemical substances used as drugs and biocides, or as building blocks for their synthesis. An application of this approach to the preparative separation of the enantiomers of a drug intermediate is also shown. Chirality 10:492–498, 1998. © 1998 Wiley‐Liss, Inc.