In-tube derivatization for determination of absolute configuration and enantiomeric purity of chiral compounds by NMR spectroscopy

Magn Reson Chem. 2017 Apr;55(4):269-273. doi: 10.1002/mrc.4419. Epub 2016 Feb 25.

Abstract

We have developed an in-tube derivatization method using commercially available polymer-supported coupling agents to prepare derivatives of chiral compounds directly in NMR tube with high yield and purity. Because the method does not require any workup or purification, the configuration and enatiopurity can be quickly determined by NMR analysis for a small amount of chiral compounds, which is critical for today's fast-paced medicinal chemistry efforts in drug discovery. The application of the method was demonstrated for the derivatization of chiral amines, alcohols, diols, amino alcohols, thiols, and carboxylic acids using various chiral derivatizing agents and coupling agents. This article also serves as a practical guide for in-tube derivatization and selection of suitable chiral derivatizing agents and coupling agents for various types of chiral compounds. Copyright © 2016 John Wiley & Sons, Ltd.

Keywords: NMR; absolute configuration; enantiomeric purity; in-tube derivatization; polymer-supported coupling agents.