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Molecules. 2012 May 9;17(5):5550-63. doi: 10.3390/molecules17055550.

Synthesis and characterization of some new C2 symmetric chiral bisamide ligands derived from chiral Feist's acid.

Author information

1
Department of Chemistry, Faculty of Science, King Saud University, Riyadh 11451, Saudi Arabia. amajid@ksu.edu.sa

Abstract

The hemilabile chiral C2 symmetrical bidentate substituted amide ligands (1R,2R)-5(a-d) and (1S,2S)-6(a-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.

PMID:
22572937
PMCID:
PMC6268764
DOI:
10.3390/molecules17055550
[Indexed for MEDLINE]
Free PMC Article

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