Whilst there are a large number of C-C bond forming reactions available for the construction of heterocycles a number of these protocols require the use of stoichiometric organometallic reagents. Since heterocycles are present in the vast majority of pharmaceutical agents the ability to forge these structures efficiently with a minimal amount of stoichiometric metallic waste is important. With this in mind we initiated a series of projects that focus on the use of [pi]-unsaturates to serve as surrogates to toxic, air and moisture sensitive nucleophilic organometallic reagents utilized in traditional C-C bond forming reactions. This has allowed us to develop catalytic couplings of vinyl azines to imines to form branched amines, to couplings of dimethylallene to isatin forming a tert-prenyl hydroxy oxindole and this neopentyl alcohol can be substituted with C-nucleophiles forming two contiguous quaternary all-carbon centers in our synthetic studies tert-prenyl indole alkaloid natural products. / text
| Identifer | oai:union.ndltd.org:UTEXAS/oai:repositories.lib.utexas.edu:2152/ETD-UT-2012-05-5084 |
| Date | 06 July 2012 |
| Creators | Grant, Christopher Donald |
| Source Sets | University of Texas |
| Language | English |
| Detected Language | English |
| Type | thesis |
| Format | application/pdf |
Page generated in 0.0016 seconds