Synthesis and Characterization of Some New C2 Symmetric Chiral Bisamide Ligands Derived from Chiral Feist’s Acid
| Autor: | Zeid A. ALOthman, Mohammad Shahidul Islam, Assem Barakat, Ahlam F. Al-Salhoob, Abdullah M.A. Al Majid |
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| Rok vydání: | 2012 |
| Předmět: |
Denticity
Resolution (mass spectrometry) Ligand Stereochemistry Butanol Organic Chemistry Pharmaceutical Science Mass spectrometry Analytical Chemistry chemistry.chemical_compound chemistry Chemistry (miscellaneous) Reagent Yield (chemistry) Drug Discovery Molecular Medicine Amine gas treating Physical and Theoretical Chemistry |
| Zdroj: | Molecules. 17:5550-5563 |
| ISSN: | 1420-3049 |
| DOI: | 10.3390/molecules17055550 |
| Popis: | The hemilabile chiral C 2 symmetrical bidentate substituted amide ligands (1 R ,2 R )- 5 a-d and (1 S ,2 S )- 6 a-d were synthesized in quantitative yield from (1 R ,2 R )-(+)-3-methylenecyclo-propane-1,2-dicarboxylic acid (1 R ,2 R )- 3 and (1 S ,2 S )-(-)-3-methylene-cyclopropane-1,2-dicarboxylic acid (1 S ,2 S )- 3 , in two steps, respectively. The chiral Feist’s acids (1 R ,2 R )- 3 and (1 S ,2 S )- 3 were obtained in good isomeric purity by resolution of trans -(±)-3-methylene-cyclopropane-1,2-dicarboxylic acid from an 8:2 mixture of tert -butanol and water, using ( R )-(+)-α-methylbenzyl amine as a chiral reagent. This process is reproducible on a large scale. All these new synthesized chiral ligands were characterized by 1 H-NMR, 13 C-NMR, IR, and mass spectrometry, as well as elemental analysis and their specific rotations were measured. These new classes of C 2 symmetric chiral bisamide ligands could be of special interest in asymmetric transformations. Keywords: resolution of Feist’s acid; bisamide ligand |
| Databáze: | OpenAIRE |
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