Assignment of the absolute configuration of hydroxy acids using 1H NMR spectroscopy: a simple and rapid approach. Issue 2 (15th February 2017)

• Record Type: Journal Article
• Authors: Mishra, Sandeep Kumar; Suryaprakash, N.
• Is Part Of: Tetrahedron, asymmetry. Volume 28:Issue 2(2017)
• Page Start: 250
• Page End: 256
• Publication Date: 2017-02-15
• Subjects: Asymmetry (Chemistry) -- Periodicals; 547.005
• DOI: 10.1016/j.tetasy.2017.01.004
• Languages: English
• ISSNs: 0957-4166

Abstract

Graphical abstract: Abstract: A simple, rapid and highly effective protocol for assigning the absolute configuration of various chiral α-hydroxy acids and their derivatives has been established by involving the coupling of 2-formylphenylboronic acid with ( R )-[1, 1-binaphthalene]-2, 2-diamine, and 2-formylphenylboronic acid with ( S )-[1, 1-binaphthalene]-2, 2-diamine as chiral derivatizing agents. The absence of aliphatic peaks from the derivatizing agent together with the large chemical shift separation between the discriminated diastereomer peaks, with a systematic change in the direction of the displacement of peaks for an enantiomer in a particular diastereomer complex, allows the unambiguous assignment of absolute configuration.