A general approach to the synthesis of densely functionalised cyclopentenols was developed to circumvent selectivity and functionalization issues often encountered when attempting to access these synthetic intermediates using the methods currently in use. A range existing reactions were expanded upon, culminating in the formation of allyl silane starting materials for an intramolecular Sakurai reaction. The protocol was adapted to grant access to 'three of the four possible diastereoisomers of the cyclopentenol product. Conditions for a combined Claisen-Sakurai reaction were established. Treatment of diaryl ethers under basic conditions was found to lead to selective formation of either the 2- or 3- allylated ketone. Exhaustive mechanistic studies led to the proposal of base mediated isomerisation-Claisen and [2,3]-Wittig-anionic oxy-Cope rearrang~ment cascade sequences
| Identifer | oai:union.ndltd.org:bl.uk/oai:ethos.bl.uk:679210 |
| Date | January 2015 |
| Creators | McAdam, Catherine |
| Publisher | Queen's University Belfast |
| Source Sets | Ethos UK |
| Detected Language | English |
| Type | Electronic Thesis or Dissertation |
Page generated in 0.0024 seconds