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

Organic Letters
Guangling BianGenjin Yang

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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Citations

May 19, 2016·Organic Letters·Huayin HuangHongjun Fan
Jul 15, 2016·The Journal of Organic Chemistry·Alexander J WagnerScott D Rychnovsky
Oct 20, 2015·Journal of the American Chemical Society·Min-Seob Seo, Hyunwoo Kim
Feb 9, 2017·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Márcio S Silva
Jul 28, 2015·Chemical Communications : Chem Comm·A LakshmipriyaN Suryaprakash
Mar 17, 2018·Chemical Communications : Chem Comm·Min-Seob SeoHyunwoo Kim
May 18, 2016·Organic & Biomolecular Chemistry·Ruixue PengXiaoming Feng
Feb 14, 2017·Organic Chemistry Frontiers : an International Journal of Organic Chemistry·Lixia FangJiaxin Zhang
Sep 12, 2018·Organic & Biomolecular Chemistry·Zhongxiang ChenLing Song
Jan 24, 2019·Organic & Biomolecular Chemistry·Liwen BaiXinxiang Lei

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