Highly Effective Configurational Assignment Using Bisthioureas as Chiral Solvating Agents in the Presence of DABCO

A highly effective 1H NMR method for determining the absolute configurations of various chiral α-hydroxyl acids and their derivatives has been developed with the use of bisthioureas (R)-CSA 1 and (S)-CSA 1 as chiral solvating agents in the presence of DABCO, giving distinguishable proton signals wit...

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Bibliographic Details
Published in:Organic letters 2015-03, Vol.17 (6), p.1369-1372
Main Authors: Bian, Guangling, Fan, Hongjun, Huang, Huayin, Yang, Shiwei, Zong, Hua, Song, Ling, Yang, Genjin
Format: Article
Language:English
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Summary:A highly effective 1H NMR method for determining the absolute configurations of various chiral α-hydroxyl acids and their derivatives has been developed with the use of bisthioureas (R)-CSA 1 and (S)-CSA 1 as chiral solvating agents in the presence of DABCO, giving distinguishable proton signals with up to 0.66 ppm chemical shift nonequivalence. Computational modeling studies were performed with Gaussian09 to reveal the chiral recognition mechanism.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.5b00030