Application of a One-Pot Friedel-Crafts Alkylation/Michael Addition Methodology to the Asymmetric Synthesis of Ergoline Derivatives - CNRS - Centre national de la recherche scientifique Accéder directement au contenu
Article Dans Une Revue European Journal of Organic Chemistry Année : 2017

Application of a One-Pot Friedel-Crafts Alkylation/Michael Addition Methodology to the Asymmetric Synthesis of Ergoline Derivatives

Christina Despotopoulou
  • Fonction : Auteur
Sean C. Mckeon
  • Fonction : Auteur
Robert Connon
  • Fonction : Auteur
Patrick J. Guiry
  • Fonction : Auteur

Résumé

Herein, we report a short and facile stereoselective route to ergoline derivatives. The key steps are a one-pot Friedel-Crafts alkylation/Michael addition sequence which, in the absence of chiral ligands, affords the trans-trans-stereoisomer in 44% yield as a racemate. Screening of a range of chiral bisoxazoline ligands allowed this sequence to proceed in 42-55% yields (six examples), with up to 99% ee. This approach allows for the first time, substitution at the C-4-position and the introduction of 3 chiral centres in one pot. An interesting, base-mediated conversion of the trans-trans-stereoisomer to the cis-cis-stereoisomer was discovered and both stereoisomers were characterized by X-ray crystallography.

Domaines

Chimie
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Dates et versions

hal-02141028 , version 1 (27-05-2019)

Identifiants

Citer

Christina Despotopoulou, Sean C. Mckeon, Robert Connon, Vincent Coeffard, Helge Mueller-Bunz, et al.. Application of a One-Pot Friedel-Crafts Alkylation/Michael Addition Methodology to the Asymmetric Synthesis of Ergoline Derivatives. European Journal of Organic Chemistry, 2017, 45, pp.6734-6738. ⟨10.1002/ejoc.201701480⟩. ⟨hal-02141028⟩
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