Synthesis and Characterization of Some New <em>C<sub>2</sub></em> Symmetric Chiral Bisamide Ligands Derived from Chiral Feist’s Acid
The hemilabile chiral <em>C<sub>2</sub></em> symmetrical bidentate substituted amide ligands (1<em>R</em>,2<em>R</em>)-<strong>5<sub>a-d</sub>&...
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| Format: | Article |
| Language: | English |
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MDPI AG
2012-05-01
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| Series: | Molecules |
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| Online Access: | http://www.mdpi.com/1420-3049/17/5/5550 |
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| author | Assem Barakat Zeid Abdullah Al-Othman Ahlam F. Al-Salhoob Abdullah M. A. Al Majid Mohammad Shahidul Islam |
| author_facet | Assem Barakat Zeid Abdullah Al-Othman Ahlam F. Al-Salhoob Abdullah M. A. Al Majid Mohammad Shahidul Islam |
| author_sort | Assem Barakat |
| collection | DOAJ |
| description | The hemilabile chiral <em>C<sub>2</sub></em> symmetrical bidentate substituted amide ligands (1<em>R</em>,2<em>R</em>)-<strong>5<sub>a-d</sub></strong> and (1<em>S</em>,2<em>S</em>)-<strong>6<sub>a-d</sub></strong> were synthesized in quantitative yield from (1<em>R</em>,2<em>R</em>)-(+)-3-methylenecyclo-propane-1,2-dicarboxylic acid (1<em>R</em>,2<em>R</em>)-<strong>3</strong> and (1<em>S</em>,2<em>S</em>)-(-)-3-methylene-cyclopropane-1,2-dicarboxylic acid (1<em>S</em>,2<em>S</em>)-<strong>3</strong>, in two steps, respectively. The chiral Feist’s acids (1<em>R</em>,2<em>R</em>)-<strong>3</strong> and<strong> </strong>(1<em>S</em>,2<em>S</em>)-<strong>3</strong> were obtained in good isomeric purity by resolution of <em>trans</em>-(±)-3-methylene-cyclopropane-1,2-dicarboxylic acid from an 8:2 mixture of <em>tert</em>-butanol and water, using (<em>R</em>)-(+)-<em>α</em>-methylbenzyl amine as a chiral reagent. This process is reproducible on a large scale. All these new synthesized chiral ligands were characterized by <sup>1</sup>H-NMR, <sup>13</sup>C-NMR, IR, and mass spectrometry, as well as elemental analysis and their specific rotations were measured. These new classes of <em>C<sub>2</sub></em> symmetric chiral bisamide ligands could be of special interest in asymmetric transformations. |
| first_indexed | 2024-12-11T22:42:15Z |
| format | Article |
| id | doaj.art-9f2adfef9ee2490eb90a05c0ac748cf8 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-12-11T22:42:15Z |
| publishDate | 2012-05-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-9f2adfef9ee2490eb90a05c0ac748cf82022-12-22T00:47:45ZengMDPI AGMolecules1420-30492012-05-011755550556310.3390/molecules17055550Synthesis and Characterization of Some New <em>C<sub>2</sub></em> Symmetric Chiral Bisamide Ligands Derived from Chiral Feist’s AcidAssem BarakatZeid Abdullah Al-OthmanAhlam F. Al-SalhoobAbdullah M. A. Al MajidMohammad Shahidul IslamThe hemilabile chiral <em>C<sub>2</sub></em> symmetrical bidentate substituted amide ligands (1<em>R</em>,2<em>R</em>)-<strong>5<sub>a-d</sub></strong> and (1<em>S</em>,2<em>S</em>)-<strong>6<sub>a-d</sub></strong> were synthesized in quantitative yield from (1<em>R</em>,2<em>R</em>)-(+)-3-methylenecyclo-propane-1,2-dicarboxylic acid (1<em>R</em>,2<em>R</em>)-<strong>3</strong> and (1<em>S</em>,2<em>S</em>)-(-)-3-methylene-cyclopropane-1,2-dicarboxylic acid (1<em>S</em>,2<em>S</em>)-<strong>3</strong>, in two steps, respectively. The chiral Feist’s acids (1<em>R</em>,2<em>R</em>)-<strong>3</strong> and<strong> </strong>(1<em>S</em>,2<em>S</em>)-<strong>3</strong> were obtained in good isomeric purity by resolution of <em>trans</em>-(±)-3-methylene-cyclopropane-1,2-dicarboxylic acid from an 8:2 mixture of <em>tert</em>-butanol and water, using (<em>R</em>)-(+)-<em>α</em>-methylbenzyl amine as a chiral reagent. This process is reproducible on a large scale. All these new synthesized chiral ligands were characterized by <sup>1</sup>H-NMR, <sup>13</sup>C-NMR, IR, and mass spectrometry, as well as elemental analysis and their specific rotations were measured. These new classes of <em>C<sub>2</sub></em> symmetric chiral bisamide ligands could be of special interest in asymmetric transformations.http://www.mdpi.com/1420-3049/17/5/5550resolution of Feist’s acidbisamide ligand<em>C<sub>2</sub> </em>symmetric |
| spellingShingle | Assem Barakat Zeid Abdullah Al-Othman Ahlam F. Al-Salhoob Abdullah M. A. Al Majid Mohammad Shahidul Islam Synthesis and Characterization of Some New <em>C<sub>2</sub></em> Symmetric Chiral Bisamide Ligands Derived from Chiral Feist’s Acid Molecules resolution of Feist’s acid bisamide ligand <em>C<sub>2</sub> </em>symmetric |
| title | Synthesis and Characterization of Some New <em>C<sub>2</sub></em> Symmetric Chiral Bisamide Ligands Derived from Chiral Feist’s Acid |
| title_full | Synthesis and Characterization of Some New <em>C<sub>2</sub></em> Symmetric Chiral Bisamide Ligands Derived from Chiral Feist’s Acid |
| title_fullStr | Synthesis and Characterization of Some New <em>C<sub>2</sub></em> Symmetric Chiral Bisamide Ligands Derived from Chiral Feist’s Acid |
| title_full_unstemmed | Synthesis and Characterization of Some New <em>C<sub>2</sub></em> Symmetric Chiral Bisamide Ligands Derived from Chiral Feist’s Acid |
| title_short | Synthesis and Characterization of Some New <em>C<sub>2</sub></em> Symmetric Chiral Bisamide Ligands Derived from Chiral Feist’s Acid |
| title_sort | synthesis and characterization of some new lt em gt c lt sub gt 2 lt sub gt lt em gt symmetric chiral bisamide ligands derived from chiral feist s acid |
| topic | resolution of Feist’s acid bisamide ligand <em>C<sub>2</sub> </em>symmetric |
| url | http://www.mdpi.com/1420-3049/17/5/5550 |
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