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Copper catalyzed conjugate addition of alkenylaluminums to unactivated substrates

Defense Thèse de doctorat : Univ. Genève, 2012 - Sc. 4502 - 2012/12/07
Abstract The main focus of this thesis is the creation of quaternary all-carbon stereogenic centers bearing an alkenyl moiety via Copper-catalyzed asymmetric conjugate addition (ACA) employing alkenyl aluminum nucleophiles. Two strategies for the generation of these nucleophiles were used (Transmetalation from the corresponding alkenylbromides and hydroalumination of alkynes) which allowed for the conjugate addition of a wide array of alkenyl groups in good yields and high enantioselectivities. Furthermore, these procedures were employed for the highly enantioselective conjugate addition of alkyl-, alkenyl- and aryl alanes to N-Substituted-2-3-dehydro-4-piperidones. Phosphinamine ligands also known as SimplePhos Ligands showed to be highly efficient for the Copper-catalyzed ACA with alkenyl aluminums. Previously reported protocols for the synthesis of these ligands involved complicated experimental procedures including protection and deprotection steps. In the course of this work an improved synthesis of chiral phosphinamine ligands was developed and new members of SimplePhos ligands were generated by a simple one-pot procedure.
Keywords CopperCatalysisEnantioselectiveAlane
URN: urn:nbn:ch:unige-258587
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MUELLER, Daniel. Copper catalyzed conjugate addition of alkenylaluminums to unactivated substrates. Université de Genève. Thèse, 2012. doi: 10.13097/archive-ouverte/unige:25858 https://archive-ouverte.unige.ch/unige:25858

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