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

Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry
Abdullah M A Al MajidAssem Barakat

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.

References

Nov 20, 2001·Chemical Reviews·L Pu, H B Yu
Apr 2, 2002·Organic Letters·Peter Wipf, Xiaodong Wang
Jul 4, 2003·Chirality·Ayako HondaPatrick J Walsh
Sep 1, 1986·Journal of the American Chemical Society·M KitamuraR Noyori

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