NMR chiral discrimination of chalcogen containing secondary alcohols. Issue 1 (15th November 2018)

• Record Type: Journal Article
• Authors: Marques, Naiade B.G.; Jacob, Raquel G.; Perin, Gelson; Lenardão, Eder J.; Alves, Diego; Silva, Márcio S.
• Is Part Of: Chirality. Volume 31:Issue 1(2019)
• Page Start: 41
• Page End: 51
• Publication Date: 2018-11-15
• Subjects: chalcogen compounds -- chiral derivatizing agent -- chiral solvating agent -- NMR discrimination -- secondary alcohols; Chirality -- Periodicals; Pharmaceutical chemistry -- Periodicals; 541.22
• DOI: 10.1002/chir.23030
• Languages: English
• ISSNs: 0899-0042

Abstract

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. Abstract :