The need for asymmetric synthesis has been outlined and methods for generating asymmetry discussed. The chemistry of the well known 2,2'-disubstituted-1,1'-binapthyl system was reviewed and a novel chiral auxiliary has been designed around this system. Modifications were implemented to introduce originality into the system and hopefully increase stereoselectivity. These included an increase in steric bulk and the introduction of different co-ordinating functionalities. A quick and efficient synthesis of a series of novel biphenanthryl compounds has been developed in four steps from commercially available starting material. Resolution was effected at an early stage in the synthesis. The resolution was confirmed by X-ray crystallography and circular dichroism. The absolute configuration of the series has also been assigned. Investigations into the possible synthesis of a BINAP analogue, the chiral modification of lithium aluminium hydride, use as a chiral auxiliary and the possible synthesis of a chiral dihydropyridine reagent are also discussed.
| Identifer | oai:union.ndltd.org:bl.uk/oai:ethos.bl.uk:640146 |
| Date | January 1996 |
| Creators | Picken, C. Louise |
| Publisher | University of Edinburgh |
| Source Sets | Ethos UK |
| Detected Language | English |
| Type | Electronic Thesis or Dissertation |
| Source | http://hdl.handle.net/1842/11253 |
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