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Heterohelicenes with Embedded P-Chiral 1H-Phosphindole or Dibenzophosphole Units: Diastereoselective Photochemical Synthesis and Structural Characterization.

Abstract : The oxidative photocyclization reactions of olefins that contain 1H-phosphindole or dibenzophosphole substituents have been applied to the synthesis of P/N-bi-heterosubstituted dimeric helicenes, as well as of new [6]- and [8]phosphahelicenes. In these photocyclization processes, the configuration of the stereogenic phosphorus center dictates the sense of helical chirality. Thus, by starting from enantiomerically pure P-menthylphosphole-oxide units, this method affords enantiopure helical compounds. The helical phosphine oxides were characterized by X-ray diffraction. After reduction of the phosphine-oxides, the corresponding helical phosphines have been used as ligands in transition-metal complexes. The X-ray crystal structure of a gold chloride complex of a [6]helicene is reported.
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https://hal.archives-ouvertes.fr/hal-00856817
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Submitted on : Monday, September 2, 2013 - 3:24:14 PM
Last modification on : Saturday, July 3, 2021 - 3:44:51 AM

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Keihann Yavari, Pascal Retailleau, Arnaud Voituriez, Angela Marinetti. Heterohelicenes with Embedded P-Chiral 1H-Phosphindole or Dibenzophosphole Units: Diastereoselective Photochemical Synthesis and Structural Characterization.. Chemistry - A European Journal, Wiley-VCH Verlag, 2013, 19 (30), pp.9939-47. ⟨10.1002/chem.201300844⟩. ⟨hal-00856817⟩

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