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Synthesis and Spectral and Structural Characterization of a New Series of Bis-Strapped Chiral Porphyrins Derived from L-Proline

Abstract : New chiral porphyrins were obtained in reasonable yields in three steps, starting from the áâáâ atropisomer of mesotetrakis(o-aminophenyl)porphyrin (TAPP). These potential catalysts for the enantioselective epoxidation of alkenes were obtained by the reaction of different linkers on the same Lprolinoyl-picket porphyrin. Their 1H NMR spectral characteristics, as well as the crystal structure of one of them, clearly indicate that the orientation of the proline cycle depends on the linker used to tether the two pickets on each side of the porphyrin. The same linker is employed for both sides of the porphyrin; hence the resulting D2-symmetric superstructure.
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https://hal-univ-rennes1.archives-ouvertes.fr/hal-01469589
Contributor : Bernard Boitrel <>
Submitted on : Thursday, February 16, 2017 - 3:38:09 PM
Last modification on : Friday, June 8, 2018 - 2:50:12 PM

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  • HAL Id : hal-01469589, version 1

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Bernard Boitrel, Valérie Baveux-Chambenoît, Philippe Richard. Synthesis and Spectral and Structural Characterization of a New Series of Bis-Strapped Chiral Porphyrins Derived from L-Proline. European Journal of Organic Chemistry, Wiley-VCH Verlag, 2001, 22, pp.4213-4221. ⟨hal-01469589⟩

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