An efficient route for the synthesis of a new highly selective and easily displaced chiral auxiliary I for the asymmetric boron-mediated aldol reaction has been developed in 5 steps from norephedrine. The novel chiral auxiliary has been shown to mediate <i>anti </i>and <i>syn</i> propionate and glycolate aldol reactions with a range of aldehydes in excellent yield (60-98%) and with good to excellent diastereoselectivity. Details of the methods which have been used to assign the absolute and relative stereochemistry of the aldol adducts are also summarised. The facile displacement of auxiliary I with a range of nucleophiles under very mild conditions to give the corresponding phosphonate esters, alcohols, acids, SNAc thiolesters and methyl esters has been demonstrated.
| Identifer | oai:union.ndltd.org:bl.uk/oai:ethos.bl.uk:650487 |
| Date | January 2008 |
| Creators | Fanjul, Sandra |
| Publisher | University of Edinburgh |
| Source Sets | Ethos UK |
| Detected Language | English |
| Type | Electronic Thesis or Dissertation |
| Source | http://hdl.handle.net/1842/10886 |
Page generated in 0.0017 seconds