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

Gao Jinhai | Zendy; Rajan Srinivasan | Zendy; Wang Bing | Zendy

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

Author(s) -

Gao Jinhai,

Rajan Srinivasan,

Wang Bing

Publication year - 2017

Publication title -

magnetic resonance in chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.483

H-Index - 72

eISSN - 1097-458X

pISSN - 0749-1581

DOI - 10.1002/mrc.4419

Subject(s) - derivatization , chemistry , chiral derivatizing agent , enantiomer , yield (engineering) , enantiomeric excess , nuclear magnetic resonance spectroscopy , proton nmr , organic chemistry , absolute configuration , chiral auxiliary , combinatorial chemistry , enantioselective synthesis , chromatography , chiral column chromatography , high performance liquid chromatography , catalysis , materials science , metallurgy

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.

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