Synthesis of Carbo[6]helicene Derivatives Grafted with Amino or Aminoester Substituents from Enantiopure [6]Helicenyl Boronates - Université de Rennes Accéder directement au contenu
Article Dans Une Revue Journal of Organic Chemistry Année : 2018

Synthesis of Carbo[6]helicene Derivatives Grafted with Amino or Aminoester Substituents from Enantiopure [6]Helicenyl Boronates

Résumé

Enantiopure carbo[6]helicenyl boronates were synthesized using a photocyclisation reaction as the key step. These compounds were further converted to various amino derivatives using copper-catalyzed azidation or amination and reductive alkylation of benzylazide by a helicenyl dichloroborane. Asymmetric Petasis condensation with glyoxylic acid and morpholine controlled by the helical chirality afforded the corresponding amino esters.

Domaines

Chimie organique
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Dates et versions

hal-01677471 , version 1 (16-04-2018)

Identifiants

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Nora Hellou, Aurélie Macé, Clothilde Martin, Vincent Dorcet, Thierry Roisnel, et al.. Synthesis of Carbo[6]helicene Derivatives Grafted with Amino or Aminoester Substituents from Enantiopure [6]Helicenyl Boronates. Journal of Organic Chemistry, 2018, 83 (1), pp.484-490. ⟨10.1021/acs.joc.7b02619⟩. ⟨hal-01677471⟩
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