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Non-stabilized nucleophiles in Cu-catalyzed asymmetric synthesis

This thesis describes the study of organozirconium reagents used in copper-catalyzed asymmetric synthesis. Explorations on the asymmetric allylic alkylation of linear substrates, the cyclic substrates and enantioselective desymmetrization of meso compounds including the oxabicyclic alkenes and meso-allyl substrates are reported here. <strong>Chapter 1</strong> has a brief overview about general methods used in asymmetric catalysis. In particular, more relevant introduction about catalytic asymmetric allylic substitution and asymmetric desymmetrization of meso compounds is given. <strong>Chapter 2</strong> describes the investigation of organozirconium reagents used in copper-catalyzed asymmetric allylic alkylation of linear substrates, and discloses a dynamic kinetic AAA system that employs cyclic allylic chlorides as substrates. <strong>Chapter 3</strong> presents the study on expanding the disclosed copper-catalyzed dynamic kinetic AAA chemistry by using more stabilized cyclic allylic phosphate substrates. Further exploration of its possible mechanisms uses substituted substrates, deuterated and enantiopure substrates are also discussed. <strong>Chapter 4</strong> demonstrates the study of organozirconium reagents used in copper-catalyzed enantioselective desymmetrization reactions. Investigation of oxabicyclic alkenes and mesoallyl substrates is reported. <strong>Chapter 5</strong> gives supporting information of this thesis.

Identiferoai:union.ndltd.org:bl.uk/oai:ethos.bl.uk:730049
Date January 2016
CreatorsYou, Hengzhi
ContributorsFletcher, Stephen P. ; You, Hengzhi
PublisherUniversity of Oxford
Source SetsEthos UK
Detected LanguageEnglish
TypeElectronic Thesis or Dissertation
Sourcehttps://ora.ox.ac.uk/objects/uuid:765cdc58-75a9-490b-b879-38b95b7b79ec

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