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Copper catalyzed conjugate addition to polyconjugated Michael acceptors

Defense Thèse de doctorat : Univ. Genève, 2012 - Sc. 4484 - 2012/10/31
Abstract 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.
Keywords CopperConjugate additionPolyconjugatedOrganometallic reagents
URN: urn:nbn:ch:unige-243828
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TISSOT, Matthieu. Copper catalyzed conjugate addition to polyconjugated Michael acceptors. Université de Genève. Thèse, 2012. doi: 10.13097/archive-ouverte/unige:24382 https://archive-ouverte.unige.ch/unige:24382

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Deposited on : 2012-12-10

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