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. 2015 Mar 20;17(6):1369-72.
doi: 10.1021/acs.orglett.5b00030. Epub 2015 Mar 9.

Highly effective configurational assignment using bisthioureas as chiral solvating agents in the presence of DABCO

Guangling Bian  1 , Hongjun Fan  2 , Huayin Huang  1 , Shiwei Yang  1 , Hua Zong  1 , Ling Song  1 , Genjin Yang  3
Affiliations

Highly effective configurational assignment using bisthioureas as chiral solvating agents in the presence of DABCO

Guangling Bian et al. Org Lett. .

Abstract

A highly effective (1)H 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.

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