77Se and 125Te NMR spectroscopy for enantiopurity determination of chalcogen amines. Issue 41 (12th October 2016)

• Record Type: Journal Article
• Authors: Oliveira, Samuel S.; Cunha, Rodrigo L.O.R.; Silva, Márcio S.
• Is Part Of: Tetrahedron letters. Volume 57:Issue 41(2016)
• Page Start: 4556
• Page End: 4559
• Publication Date: 2016-10-12
• Subjects: Nuclear Magnetic Resonance -- Chalcogen amines -- Chiral discrimination; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2016.08.091
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: Enantiodifferentiation of chiral chalcogen primary amines. Application of 77 Se and 125 Te nuclei in NMR chiral discrimination. Useful NMR procedure for crowed 1 H NMR spectra or large molecules. Application of HSQC 2D NMR spectroscopy in the chiral discrimination. Self-aggregation study of chalcogen–imine-boronate ester complex. Abstract: A simple three-component chiral derivatizing protocol for determining the enantiopurity of chalcogen amines by 1 H, 77 Se and 125 Te NMR spectroscopy is described. The method involves the formation of a chalcogen–imino-boronate ester complex by the coupling of racemic chalcogen amines, 2-formylphenylboronic acid and optically active (+)-BINOL. The chalcogen primary amines were synthesized by a non-active aziridine ring-opening reaction and chalcogen nucleophilic species.