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

Abstract : 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.
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https://hal.archives-ouvertes.fr/hal-01677471
Contributor : Pierre-Antoine Bouit Connect in order to contact the contributor
Submitted on : Monday, April 16, 2018 - 9:38:47 AM
Last modification on : Tuesday, May 17, 2022 - 4:36:35 PM

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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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