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Enantioselective copper catalyzed allylic alkylation using Grignard reagents; Applications in synthesis

By Anthoni Wouter van Zijl

Abstract

Enantioselective copper catalyzed allylic alkylation is a powerful carbon-carbon bond forming reaction. In this thesis the development of a new catalyst for the use of Grignard reagents in this reaction is described. This catalyst is based on copper and the ligand Taniaphos. The high regio- and enantioselectivity obtained, in particular with the introduction of a CH3 group, makes the new catalyst complementary to those reported previously for this reaction. In addition, the enantioselective copper catalyzed allylic alkylation was applied in the synthesis of relevant organic compounds, such as building blocks containing two functional groups, pheromones and heterocyclic compounds. This demonstrates that this reaction can make a valuable contribution to the possibilities that synthetic organic chemists have. In part due to this work, they might decide on applying asymmetric catalytic methods instead of older and less efficient methods, when they wish to synthesize chiral compounds, such as for instance medicinal compounds.

Topics: Stereoselectiviteit, Koperverbindingen,, Grignardverbindingen , Alkylering , Thio-ethers, Fosfininen,; Symmetrie; Proefschriften (vorm); fysische organische chemie
Year: 2009
OAI identifier: oai:ub.rug.nl:dbi/4938fdb199b72
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