Synthesis and Spectral and Structural Characterization of a New Series of Bis-Strapped Chiral Porphyrins Derived from L-Proline - Archive ouverte HAL Access content directly
Journal Articles European Journal of Organic Chemistry Year : 2001

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.

Dates and versions

hal-01469589 , version 1 (16-02-2017)

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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, 2001, 22, pp.4213-4221. ⟨10.1002/1099-0690(200111)2001%3A22<4213%3A%3AAID-EJOC4213>3.0.CO%3B2-P⟩. ⟨hal-01469589⟩
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