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Title: Synthesis and evaluation of some new terpene-based chiral auxiliaries and catalysts
Author: Doyle, Allan A.
Awarding Body: University of Edinburgh
Current Institution: University of Edinburgh
Date of Award: 1995
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The work described in this thesis has been primarily concerned with the synthesis of a number of different and novel chiral auxiliaries. All of the chosen synthetic routes to the desired auxiliaries utilised cheap and readily available terpenes from the "chiral pool". The utility of the successfully synthesised auxiliaries was evaluated in a range of asymmetric transformations, Lewis-acid catalysed Diels-Alder cycloadditions, 1,4-conjugate additions, boron enolate mediated aldol reactions and acylation reactions. The most successful auxiliaries were found to be two homologous camphor-based oxazolidin -2-one auxiliaries both of which were shown to impart excellent levels of asymmetric induction in all of the aforementioned reactions. In addition to chiral auxiliaries, some investigations were carried out on the development of camphor-derived chiral catalysts. The utility of these oxazaborolidine catalysts in asymmetric Diels-Alder cycloadditions and asymmetric ketone reduction reactions was then evaluated. It was found that neither catalyst imparted any stereoselectivity in the Diels-Alder reactions and only very low levels were observed in ketone reductions.
Supervisor: Not available Sponsor: Not available
Qualification Name: Thesis (Ph.D.) Qualification Level: Doctoral
EThOS ID:  DOI: Not available