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Title: The development of new metallo-organocatalytic reactions for asymmetric synthesis and towards the total synthesis of myrobotinol
Author: Cox, D. K.
Awarding Body: University of Cambridge
Current Institution: University of Cambridge
Date of Award: 2011
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This thesis describes studies towards the development of novel tandem transition metal-organocatalytic processes towards new chemical transformations. In particular, catalytically generated enamines have been used to capture an electrophilic palladium(II) source; initial observations of the Saegusa-type oxidation of simple aldehydes led to efforts towards intercepting the hypothesized σ-bound palladium intermediate with species such as boronic acids and carbon-carbon double bonds, to develop new asymmetric reactions. (Fig 212A) An organocatalytic a-arylation of aldehydes was then developed using catalytically generated enamines which undergo conjugate addition reactions with quinonimines, generated in situ from their parent para-aminophenols. This methodology was then applied towards the total synthesis of (-)-dehydrodiconiferyl alcohol. The total synthesis of myrobotinol was the investigated, whereby this complex molecule would be synthesized via a common precursor. This key intermediate would stem the synthesis of two fragments which would unite to furnish myrobotinol following a cascade reaction sequence. The common precursor was successfully made and work is ongoing in the laboratory to complete the synthesis of this architecturally interesting molecule.
Supervisor: Not available Sponsor: Not available
Qualification Name: Thesis (Ph.D.) Qualification Level: Doctoral
EThOS ID:  DOI: Not available