Literature DB >> 25751415

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

Guangling Bian1, Hongjun Fan2, Huayin Huang1, Shiwei Yang1, Hua Zong1, Ling Song1, Genjin Yang3.   

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.

Entities:  

Year:  2015        PMID： 25751415     DOI： 10.1021/acs.orglett.5b00030

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  7 in total

1.  Discrimination of Enantiomers of Dipeptide Derivatives with Two Chiral Centers by Tetraaza Macrocyclic Chiral Solvating Agents Using 1H NMR Spectroscopy.

Authors:  Lixia Fang; Caixia Lv; Guo Wang; Lei Feng; Pericles Stavropoulos; Guangpeng Gao; Lin Ai; Jiaxin Zhang
Journal:  Org Chem Front       Date:  2016-09-30       Impact factor: 5.281

Review 2.  Recent Advances in Multinuclear NMR Spectroscopy for Chiral Recognition of Organic Compounds.

Authors:  Márcio S Silva
Journal:  Molecules       Date:  2017-02-07       Impact factor: 4.411

3.  Azaheterocyclic diphenylmethanol chiral solvating agents for the NMR chiral discrimination of alpha-substituted carboxylic acids.

Authors:  Gao-Wei Li; Xiao-Juan Wang; Dan-Dan Cui; Yu-Fei Zhang; Rong-Yao Xu; Shuai-Hua Shi; Lan-Tao Liu; Min-Can Wang; Hong-Min Liu; Xin-Xiang Lei
Journal:  RSC Adv       Date:  2020-09-18       Impact factor: 4.036

4.  Bis-Thiourea Chiral Sensor for the NMR Enantiodiscrimination of N-Acetyl and N-Trifluoroacetyl Amino Acid Derivatives.

Authors:  Alessandra Recchimurzo; Federica Balzano; Gloria Uccello Barretta; Luca Gherardi
Journal:  J Org Chem       Date:  2022-09-05       Impact factor: 4.198

5.  Discrimination of enantiomers of amides with two stereogenic centers enabled by chiral bisthiourea derivatives using 1H NMR spectroscopy.

Authors:  Hanchang Zhang; Hongmei Zhao; Jie Wen; Zhanbin Zhang; Pericles Stavropoulos; Yanlin Li; Lin Ai; Jiaxin Zhang
Journal:  Org Biomol Chem       Date:  2021-08-05       Impact factor: 3.890

6.  Chirality sensing of tertiary alcohols by a novel strong hydrogen-bonding donor - selenourea.

Authors:  Guangling Bian; Shiwei Yang; Huayin Huang; Hua Zong; Ling Song; Hongjun Fan; Xiaoqiang Sun
Journal:  Chem Sci       Date:  2015-10-20       Impact factor: 9.825

7.  Optically Pure Aziridin-2-yl Methanols as Readily Available 1H NMR Sensors for Enantiodiscrimination of α-Racemic Carboxylic Acids Containing Tertiary or Quaternary Stereogenic Centers.

Authors:  Martyna Malinowska; Szymon Jarzyński; Adam Pieczonka; Michał Rachwalski; Stanisław Leśniak; Anna Zawisza
Journal:  J Org Chem       Date:  2020-09-02       Impact factor: 4.354
  7 in total

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