NMR chiral discrimination of chalcogen containing secondary alcohols |
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Authors: | Naiade BG Marques Raquel G Jacob Gelson Perin Eder J Lenardo Diego Alves Mrcio S Silva |
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Institution: | Naiade B.G. Marques,Raquel G. Jacob,Gelson Perin,Eder J. Lenardão,Diego Alves,Márcio S. Silva |
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Abstract: | 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 1H, 77Se‐{1H}, and 125Te‐{1H} NMR spectroscopy. A simple model for the assignment of the absolute configuration from NMR data is presented. |
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Keywords: | chalcogen compounds chiral derivatizing agent chiral solvating agent NMR discrimination secondary alcohols |
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