Use this URL to cite or link to this record in EThOS:
Title: Ketone synthesis via rhodium-catalyzed traceless chelation-controlled hydroacylation reactions
Author: Gao, Ming
ISNI:       0000 0004 7232 8320
Awarding Body: University of Oxford
Current Institution: University of Oxford
Date of Award: 2018
Availability of Full Text:
Access from EThOS:
Full text unavailable from EThOS. Restricted access.
Access from Institution:
This thesis documents the development of rhodium-catalyzed traceless chelation-controlled hydroacylation reactions for the synthesis of a variety of ketone products. Chapter 1 provides an overview of rhodium-catalyzed hydroacylation chemistry, focusing on the origin of chelation-controlled strategies and the benefits thereof. Chapter 2 describes a sequential reaction involving alkene hydroacylation, sulfide elimination and boronic acid conjugate addition, which affords products with the initial sulfide coordinating group replaced by a stereochemically defined aryl group. Chapter 3 demonstrates a sequential process involving alkyne hydroacylation, boronic acid conjugate addition and sulfide elimination, which provides enantioenriched β'-arylα,β-unsaturated ketones in a highly efficient and selective manner. Chapter 4 illustrates a versatile chelating group, triazene, for hydroacylation reactions. Subsequent functionalization of aromatic C-H bonds, promoted by the same chelating unit, offers highly substituted phenyl ketone products. Chapter 5 documents experimental procedures and data.
Supervisor: Willis, Michael C. Sponsor: Not available
Qualification Name: Thesis (Ph.D.) Qualification Level: Doctoral
EThOS ID:  DOI: Not available
Keywords: Rhodium Catalysis ; Chemistry, Organic ; Hydroacylation ; asymmetric catalysis ; cascade reaction ; rhodium catalyst