Determination of Absolute Configurations of Amines and Amino Acids Using Nonchiral Derivatizing Agents (NCDA) and Deuterium NMR

Enantiomeric analysis and empirical determination of the absolute configuration of amines and amino acids can be easily performed using acetyl-d 3 chloride as a nonchiral derivatizing agent (deuterium probe) and deuterium NMR in a chiral solvent (Courtieu's method). In the case of amino acids,...

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Bibliographic Details
Published inOrganic letters Vol. 2; no. 16; pp. 2431 - 2434
Main Authors Chalard, Pierre, Bertrand, Magali, Canet, Isabelle, Théry, Vincent, Remuson, Roland, Jeminet, Georges
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 10.08.2000
Amer Chemical Soc
Subjects
Amines - chemistry
Amino Acids - chemistry
Chemistry
Chemistry, Organic
Chymotrypsin
Deuterium
Indicators and Reagents
Magnetic Resonance Spectroscopy - methods
Molecular Conformation
Physical Sciences
Science & Technology
Stereoisomerism
H-1-NMR
REAGENT
LYOTROPIC LIQUID-CRYSTAL
ENANTIOMERIC ANALYSIS
ASSIGNMENT
CHIRAL PRIMARY AMINES
MTPA
AMIDES
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Summary:Enantiomeric analysis and empirical determination of the absolute configuration of amines and amino acids can be easily performed using acetyl-d 3 chloride as a nonchiral derivatizing agent (deuterium probe) and deuterium NMR in a chiral solvent (Courtieu's method). In the case of amino acids, derivatization to amido esters, performed with methanol-d 4 and acetyl-d 3 chloride, gives a double opportunity for enantiomeric analysis.
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ISSN:1523-7060
1523-7052
DOI:10.1021/ol006066g