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Steric hindrance influence on the enantiorecognition ability of tyrosine‐derived chiral stationary phases
Author(s) -
Siret L.,
Tambuté A.,
Bégos A.,
Rouden J.,
Caude M.
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.530030509
Subject(s) - chemistry , substituent , steric effects , enantiomer , isopropyl , stereoselectivity , amide , stereochemistry , medicinal chemistry , organic chemistry , catalysis
Four chiral stationary phases (CSPs) derived from N ‐(3,5‐dinitrobenzoyl)tyrosine have been synthesized. They differ by the substituent nature (methyl, ethyl, isopropyl, tert ‐butyl) of the aliphatic amide function. The enantiorecognition ability of these CSPs was evaluated with 10 racemates. For the majority of them, the stereoselectivity increases with the steric hindrance of the substituent. The chiral selector enantiomeric separation on the resulting CSPs has evidenced a reversal of elution order only for CS 4 on CSP 4 ( tert ‐butyl substituent), suggesting a change in its conformation.