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Chalcogen‐Containing Diols: A Novel Chiral Derivatizing Agent for 77 Se and 125 Te NMR Chiral Recognition of Primary Amines
Author(s) -
Lima Yanka Rocha,
Peglow Thiago Jacobsen,
Nobre Patrick Carvalho,
Campos Patrick Teixeira,
Perin Gelson,
Lenardão Eder J.,
Silva Márcio S.
Publication year - 2019
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201900097
Subject(s) - diastereomer , chiral derivatizing agent , enantiopure drug , chemistry , tellurium , enantiomer , nuclear magnetic resonance spectroscopy , chalcogen , diol , reagent , selenium , derivatization , organic chemistry , chiral column chromatography , stereochemistry , enantioselective synthesis , high performance liquid chromatography , catalysis
In this work, a novel chiral diol containing a chalcogen was developed for the 77 Se and 125 Te NMR chiral recognition of racemic primary amines. The enantiopure chiral derivatizing agents were synthesized from a readily available and versatile ( S )‐solketal reagent. The synthesis was performed in three steps with satisfactory yields. The chiral derivatizing agents containing selenium or tellurium nuclides were evaluated for effective NMR chiral discrimination of racemic primary amines by a simple three component chiral derivatization protocol through the modified James‐Bull method. The split 77 Se and 125 Te NMR signals are well‐distinguishable and greater than 1 H NMR signals. The Nuclear Overhauser Spectroscopy (NOESY) NMR 2D analysis and semi‐empirical method suggest a conformational preference of diastereoisomers, that provide information of the absolute configuration using selenium and tellurium chiral derivatizing agents.