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NMR chiral discrimination of chalcogen containing secondary alcohols
Author(s) -
Marques Naiade B.G.,
Jacob Raquel G.,
Perin Gelson,
Lenardão Eder J.,
Alves Diego,
Silva Márcio S.
Publication year - 2019
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.23030
Subject(s) - chalcogen , chemistry , absolute configuration , chiral derivatizing agent , ternary operation , nuclear magnetic resonance spectroscopy , proton nmr , organic chemistry , combinatorial chemistry , stereochemistry , enantiomer , chiral column chromatography , computer science , programming language
Here, we report the general strategies by which NMR spectroscopy can be used to determine the enantiopurity and absolute configuration of chalcogen containing secondary alcohols, including the evaluation of the use of chiral solvating and chiral derivatizing agents. The BINOL/DMAP ternary complex demonstrated a simple and fast protocol for determining enantiopurity. The drug Naproxen afforded a stable, nonhygroscopic, and readily available chiral derivatizing agent (CDA) for NMR chiral discrimination of chalcogen containing secondary alcohols. The chiral recognition by CDA and chiral solvating agent (CSA) was assessed using 1 H, 77 Se‐{1H}, and 125 Te‐{1H} NMR spectroscopy. A simple model for the assignment of the absolute configuration from NMR data is presented.