Carbon-carbon bond formation is one the fundamental reactions in organic
synthesis. The quest for the development of new and more efficient processes for the
construction of this bond has been an ongoing focus for years. The transformations that
permit the use of simple precursors to access complex structural architectures in the
absence of stoichiometric quantities by-products are highly desirable.
Hydrogen is a cheapest and cleanest reductant available to the mankind. The
catalytic hydrogenation has been widely utilized in the industry, however the construction
of the carbon-carbon bond under hydrogenative conditions has been achieved only for
alkene hydroformylations and Fisher-Tropsh process and limited to the use of carbon
monoxide. The extension of the hydrogenative carbon-carbon bond formations beyond
aforementioned processes would be of a great significance to the synthetic community.
The overview of allene use in the metal catalyzed reactions to achieve carbonyl
and imine allylation and vinylation is presented in Chapter 1. The following chapter
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discusses the development of metal catalyzed hydrogenative and transfer hydrogenative
coupling of allenes and carbonyl compounds to afford allylation products. These studies
have resulted in the development of the first carbonyl allylation from the alcohol
oxidation level. Chapter 3 discusses efforts towards achieving highly enantioselective
hydrogenative coupling of alkynes to carbonyl compounds. / text
| Identifer | oai:union.ndltd.org:UTEXAS/oai:repositories.lib.utexas.edu:2152/ETD-UT-2009-12-444 |
| Date | 24 August 2010 |
| Creators | Skucas, Eduardas |
| Contributors | Krische, Michael J. |
| Source Sets | University of Texas |
| Language | English |
| Detected Language | English |
| Type | thesis |
| Format | application/pdf |
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