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Molecules 2012, 17(5), 5550-5563; doi:10.3390/molecules17055550
Article

Synthesis and Characterization of Some New C2 Symmetric Chiral Bisamide Ligands Derived from Chiral Feist’s Acid

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Received: 7 February 2012; in revised form: 16 April 2012 / Accepted: 20 April 2012 / Published: 9 May 2012
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Abstract: The hemilabile chiral C2 symmetrical bidentate substituted amide ligands (1R,2R)-5a-d and (1S,2S)-6a-d were synthesized in quantitative yield from (1R,2R)-(+)-3-methylenecyclo-propane-1,2-dicarboxylic acid (1R,2R)-3 and (1S,2S)-(-)-3-methylene-cyclopropane-1,2-dicarboxylic acid (1S,2S)-3, in two steps, respectively. The chiral Feist’s acids (1R,2R)-3 and (1S,2S)-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 1H-NMR, 13C-NMR, IR, and mass spectrometry, as well as elemental analysis and their specific rotations were measured. These new classes of C2 symmetric chiral bisamide ligands could be of special interest in asymmetric transformations.
Keywords: resolution of Feist’s acid; bisamide ligand; C2 symmetric resolution of Feist’; s acid; bisamide ligand; C2 symmetric
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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MDPI and ACS Style

Al Majid, A.M.A.; Islam, M.S.; Al-Othman, Z.A.; Al-Salhoob, A.F.; Barakat, A. Synthesis and Characterization of Some New C2 Symmetric Chiral Bisamide Ligands Derived from Chiral Feist’s Acid. Molecules 2012, 17, 5550-5563.

AMA Style

Al Majid AMA, Islam MS, Al-Othman ZA, Al-Salhoob AF, Barakat A. Synthesis and Characterization of Some New C2 Symmetric Chiral Bisamide Ligands Derived from Chiral Feist’s Acid. Molecules. 2012; 17(5):5550-5563.

Chicago/Turabian Style

Al Majid, Abdullah M. A.; Islam, Mohammad Shahidul; Al-Othman, Zeid A.; Al-Salhoob, Ahlam F.; Barakat, Assem. 2012. "Synthesis and Characterization of Some New C2 Symmetric Chiral Bisamide Ligands Derived from Chiral Feist’s Acid." Molecules 17, no. 5: 5550-5563.


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