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Thèse
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Copper catalyzed conjugate addition to polyconjugated Michael acceptors

Contributeurs/tricesTissot, Matthieu
Directeurs/tricesAlexakis, Alexandre
Date de soutenance2012-10-31
Résumé

Copper catalysed conjugate addition is one of the most powerful methods for the creation of the C-C bond as part of the quest to develop new synthetic routes towards the generation of specific chiral centers. In this Ph.D work, our objective was to extend the asymmetric conjugate addition (ACA), to a new class of challenging substrates, the polyconjugated Michael acceptors. The main challenge with this class of substrates is to control the regioselectivity and the enantioselectivity. We discovered that many factors influenced the regioselectivity trends, such as the electronic and the steric properties of the Michael acceptors. Also an important dependence on the nature of the nucleophilic species was observed. By choosing appropriate combination of parameters, we developed various methodologies allowing the selective 1,4- or 1,6-addition with high level of enantiocontrol. We also demonstrated the synthetic value of those methodologies by synthesizing valuable building blocks bearing quaternary stereogenic centers.

eng
Mots-clés
  • Copper
  • Conjugate addition
  • Polyconjugated
  • Organometallic reagents
Citation (format ISO)
TISSOT, Matthieu. Copper catalyzed conjugate addition to polyconjugated Michael acceptors. 2012. doi: 10.13097/archive-ouverte/unige:24382
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Informations techniques

Création10/12/2012 14:16:00
Première validation10/12/2012 14:16:00
Heure de mise à jour14/03/2023 17:46:38
Changement de statut14/03/2023 17:46:38
Dernière indexation29/01/2024 19:37:08
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