A review covering the literature until April 2008 concerning organometallic reactions to funcionalise oxazoles is described. A protocol for the functionalisation of the oxazole 2- and 4-positions using the Suzuki coupling reaction is described. 2- Aryl-4-trifloyloxazoles undergo rapid, microwave-assisted coupling with a range of aryl and heteroaryl boronic acids in good to excellent yields. The methodology is similarly effective using 4-aryl-2-chlorooxazoles as the coupling partner and has been extended to the synthesis of a novel class of homo- and heterodimeric 4,4- linked dioxazoles. In addition, a regioselective Suzuki-Miyaura cross-coupling of 2,4-dihalooxazoles followed by a Stille coupling has been successfully developed. The procedure affords convergent syntheses of trisoxazoles in high yield and in a minimum number of steps. Furthermore, C-2 direct arylation of oxazoles is discussed. This methodology is extended to the synthesis of C2-C4’ linked bis and tris oxazoles of the type found in the Ulapualide A family of natural products.
| Identifer | oai:union.ndltd.org:bl.uk/oai:ethos.bl.uk:562254 |
| Date | January 2008 |
| Creators | Flegeau, Emmanuel Ferrer |
| Contributors | Greaney, Michael F. |
| Publisher | University of Edinburgh |
| Source Sets | Ethos UK |
| Detected Language | English |
| Type | Electronic Thesis or Dissertation |
| Source | http://hdl.handle.net/1842/3171 |
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