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Enantioselective separation of enantiomeric amides on three amylose‐based chiral stationary phases: Effects of backbone and carbamate side chain chiralities
Author(s) -
Booth Tristan D.,
Lough W. John,
Saeed Mansoor,
Noctor Terrence A.G.,
Wainer Irving W.
Publication year - 1997
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(1997)9:2<173::aid-chir18>3.0.co;2-k
Subject(s) - chemistry , chirality (physics) , amylose , enantiomer , carbamate , enantioselective synthesis , side chain , chromatography , organic chemistry , stereochemistry , starch , polymer , catalysis , physics , chiral symmetry breaking , quantum mechanics , nambu–jona lasinio model , quark
A series of enantiomeric amides have been chromatographed on three amylose‐based chiral stationary phases (CSPs): amylose tris(3,5‐dimethylphenylcarbamate) (AD‐CSP), amylose tris (S‐phenylethylcarbamate) (AS‐CSP), and amylose tris(R‐phenylethyl‐carbamate) (AR‐CSP). The relative retentions and enantioselectives of the solutes on the three CSPs were compared and basic structure‐retention relationships developed to describe the chromatographic results. The data indicate that for these solutes the observed elution order was a function of the chirality of the amylose backbone, while the magnitude of the enantioselective separations was affected by the chirality of the carbamate side chain. Chirality 9:173–177, 1997. © 1997 Wiley‐Liss, Inc.