NMR chiral discrimination of chalcogen containing secondary alcohols

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 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.

Keywords: NMR discrimination; chalcogen compounds; chiral derivatizing agent; chiral solvating agent; secondary alcohols.