New Chiral Diamide Ligands Containing Redox‐Active Hydroquinone Groups. Synthesis and Results in the Palladium(II)‐Catalyzed 1,4‐Diacetoxylation of 1,3‐Dienes.

Verboom, Renzo C.; Plietker, Bernd; Baeckvall, Jan‐E.

doi:10.1002/chin.200416097

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“…Over the past few decades, C 2 symmetric chiral amides and sulfonamides have proven to be efficient ligands for several asymmetric transformations [1,2,3,4], due to their great potential of binding with the metal alkoxides, especially with Ti(IV) alkoxides, through the nitrogen atom. Therefore considerable efforts have been devoted to the synthesis of a variety of substituted C 2 symmetric chiral amide ligands [5,6,7,8]. Recently a series of new chiral sulfonamides with a rigid cyclohexyl backbone were introduced by Wals and co-workers for the asymmetric addition of diethyl zinc to aldehydes [8].…”

Section: Introductionmentioning

confidence: 99%

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

et al. 2012

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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.

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