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A CD Exciton Chirality Method for Determination of the Absolute Configuration of t hreo-β-Aryl-β-hydroxy-α-amino Acid Derivatives

The absolute configuration of threo-β-aryl-β-hydroxy-α-amino acids was studied by CD exciton chirality method using 7-diethylaminocoumarin-3-carboxylate as a red-shifted chromophore. Bischromophoric derivatives for a series of threo-β-aryl-β-hydroxy-α-amino acids (3a−h) were prepared and their CD sp...

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Bibliographic Details
Published in:Journal of organic chemistry 2002-02, Vol.67 (4), p.1368-1371
Main Authors: Lo, Lee-Chiang, Yang, Chun-Tzu, Tsai, Charng-Sheng
Format: Article
Language:English
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Summary:The absolute configuration of threo-β-aryl-β-hydroxy-α-amino acids was studied by CD exciton chirality method using 7-diethylaminocoumarin-3-carboxylate as a red-shifted chromophore. Bischromophoric derivatives for a series of threo-β-aryl-β-hydroxy-α-amino acids (3a−h) were prepared and their CD spectra measured in CH2Cl2. By combining the data of CD and NMR coupling constants, we are able to correlate their preferred conformer (B) and the positive CD to the corresponding (2S,3R)-absolute configuration. These results are consistent with those obtained from serine and threonine derivatives, which represent the simplest form of β-hydroxy-α-amino acids. This CD method could thus become a general method for determining the absolute configuration of threo-β-aryl-β-hydroxy-α-amino acids.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo016070l